Recycling process for a multilayer system

Abstract

Recycling Method for a Multilayer System. The present invention relates to the use of a multilayer system F1 comprising: a layer C1 comprising at least one polyolefin, an adhesive layer A comprising the reaction product between a –NCO component and an –OH component, and a layer C2 comprising at least one polyolefin, to prepare a recycled article, said multilayer system F1 comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system. Figure: None

Description

Title of the invention: Method for recycling a multi-layer system FIELD OF INVENTION

[0001] The present invention relates to a method for recycling a specific multilayer system.

[0002] The present invention also relates to the use of a multilayer system to prepare a recycled article. TECHNOLOGICAL BACKGROUND

[0003] Multilayer articles (or laminated articles) are used in many fields for packaging a wide variety of products, particularly in the food, cosmetics, and detergent industries. Depending on the requirements, these articles can be flexible or rigid. They are notably used for flexible packaging. These articles are generally made of different materials (composite multilayer articles). The materials can be chosen from paper, metal, or thermoplastic polymers. Thermoplastic polymers can be chosen from polyethylene (PE), polypropylene (PP), ethylene-vinyl acetate copolymers (EVA), polyamide (PA), polyethylene terephthalate (PET), polyvinyl chloride (PVC), polyvinylidene fluoride (PVDF), lactic acid polymers (PLA), polyhydroxyalkanoate (PHA), or mixtures thereof.

[0004] An individual layer of material can itself be made up of several materials. It can be, for example, a layer of thermoplastic polymers obtained by co-extrusion of two polymers (there is then no glue between the co-extruded layers), the individual layers of thermoplastic polymer can in addition be coated with a substance (for example based on aluminium oxide or silicon oxide), a protein layer or metallized (metallization with aluminium particles) to add an additional barrier effect.

[0005] The characteristics and properties of multilayer articles will depend in particular on the materials used to obtain the layers. Thus, it is common to combine layers comprising different materials in order to obtain multilayer articles, most commonly composite multilayer articles, combining the characteristics and properties of the different individual layers and therefore having particular characteristics and properties, for example in terms of visual appearance, barrier properties to gas and moisture, safety or lack of toxicity for users, inertness with respect to packaged products, chemical resistance to packaged products and / or physical, mechanical resistance, thermal and chemical processes related to manufacturing and packaging.

[0006] The layers can be assembled by bonding using lamination processes. These lamination processes can be implemented using adhesive compositions or suitable devices.

[0007] Today, there is a wide variety of multilayer articles with characteristics and properties suited to multiple uses. However, these articles generally have the disadvantage of being single-use and generating waste. In order to meet the climate challenge, reduce environmental pollution, conserve natural resources, and adapt to more stringent regulations, it is imperative to develop recycling and recovery channels for this waste.

[0008] Despite the development of various recycling and recovery channels, many multilayer articles are difficult to recycle due to reasons of yield, technical feasibility, performance, cost, etc. For example, the recycled materials obtained do not necessarily have the characteristics and properties required for producing new articles such as films: presence of gels / unmelted material impacting the visual quality of the recycled article, deterioration of mechanical and / or physical properties, incompatibility, turbidity, discoloration, etc.

[0009] There is therefore a need for new solutions to remedy at least some of these drawbacks.

[0010] There is therefore a real need to supply multilayer articles that can be recycled, particularly mechanically, to produce recycled articles with satisfactory mechanical and physicochemical properties and characteristics. There is also a need to supply recycled articles comprising a significant proportion of recycled materials, while still having satisfactory mechanical and physicochemical properties and characteristics. DESCRIPTION OF THE INVENTION Use of a multilayer Fl system

[0011] The present invention relates to the use of a multilayer Fl system comprising: - a Cl layer comprising at least one polyolefin, - an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, - a C2 layer comprising at least one polyolefin,

[0012] to prepare a recycled article,

[0013] said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system.

[0014] The multilayer system Fl necessarily includes at least these three layers Cl, C2 and A.

[0015] In the context of the present invention, "article", "structure" and "system" are used interchangeably.

[0016] The multilayer system Fl can be a laminate, a complex, a film.

[0017] Advantageously, the Fl multilayer system is mechanically recyclable.

[0018] The term "mechanically recyclable" is used to indicate that the Fl multilayer system can be converted into a new article via a mechanical recycling process.

[0019] Mechanical recycling has been known for many years. From an environmental perspective, mechanical recycling (compared to chemical recycling) is the most energy-efficient and generates little waste. Chemical recycling is defined in particular by ISO 15270 as the conversion into monomers or the production of new raw materials by modifying the chemical structure of plastic waste through cracking, gasification, or depolymerization, excluding energy recovery and incineration.

[0020] For the purposes of this invention, "mechanical recycling" means the definition given in ISO 15270, namely the processing of plastic waste into secondary raw materials or products without significant modification of the chemical structure of the material, for example, without modification of the chemical functions and repeating patterns. Mechanical recycling includes at least one mechanical grinding step.

[0021] In the context of the invention, the terms "recycled" and "recycled" refer to a material derived at least in part from either post-consumer waste or industrial waste. Post-consumer waste refers to items that have already been used by the consumer at least once (i.e., they have served their original purpose), while industrial waste refers to manufacturing residues that do not reach the consumer. Manufacturing residues can be, for example, the offcuts from rolls of multilayer composites when they are cut after production to prepare packaging.

[0022] In the context of the invention, the term "virgin" refers to newly produced materials and / or articles before their first use and not having been recycled. Cl and C2 layers

[0023] The Cl layer may comprise a polyolefin or a mixture of polyolefins.

[0024] The C2 layer may comprise a polyolefin or a mixture of polyolefins.

[0025] The Cl and C2 layers may comprise one or more polyolefins of identical or different chemical nature.

[0026] An example of polyolefins of the same chemical nature (same composition) chemical) is: the Cl layer comprising a polyethylene and the C2 layer comprising a polyethylene.

[0027] The Cl and C2 layers may comprise one or more polyolefins having different physico-chemical characteristics.

[0028] An example of polyolefins of the same chemical nature (same chemical composition) but with different physicochemical characteristics is: layer C1 comprises low-density polyethylene, layer C2 comprises high-density polyethylene. Thus, the chemical nature is identical: polyethylene, but the physicochemical characteristics such as density are different.

[0029] An example of polyolefins of different chemical nature (chemical composition) is: the Cl layer comprising a polyethylene, and the C2 layer comprising a polypropylene.

[0030] The physico-chemical characteristics of the Cl and C2 layers may be different, for example due to differences in the molecular weight of the polyolefin(s), the degree of branching of the polyolefin(s), the density of the polyolefin(s), the thickness of the layer, the orientation of the polyolefin(s), etc.

[0031] The Cl and C2 layers may comprise one or more identical or different polyolefins.

[0032] When layer Cl (respectively C2) comprises a mixture of polyolefins, these can be in the form of different layers: for example a polyethylene layer and a polypropylene layer, corresponding to a polyethylene / polypropylene mixture, or layer Cl is a single layer comprising a mixture of several polyolefins.

[0033] The term “polyolefin” covers homopolymers and copolymers prepared from olefin monomers.

[0034] Copolymers include, in particular:

[0035] - copolymers obtained from at least two different olefins (for example ethylene-propylene or ethylene-butene copolymers), and

[0036] - copolymers obtained from at least one olefin monomer with at least one co-monomer, said copolymers comprising more than 50 mol% of units derived from olefin monomer(s).

[0037] Each of the Cl and C2 layers can comprise, independently of each other, a polyolefin selected from polyethylene (PE), polypropylene (PP), ethylene-propylene copolymers, and mixtures thereof; preferably, a polyolefin selected from PE, PP, and mixtures thereof.

[0038] Polyethylene can be chosen from a linear polyethylene such as HDPE (“High Density Polyethylene”), a linear low-density polyethylene (LLDPE, Linear low-density polyethylene (LLDPE), very low-density polyethylene (VLDPE), ultra-low-density polyethylene (ULDPE), branched polyethylene such as low-density polyethylene (LDPE), and medium-density polyethylene (MDPE). Such polyethylenes can be prepared by several methods, including polymerization in the presence of a Ziegler-Natta catalyst, metallocene-catalyzed polymerization, or radical polymerization.

[0039] HDPEs may, in particular, have a density ranging from 0.940 to 0.970 g / cm³.

[0040] ULDPEs may, in particular, have a density ranging from 0.890 to 0.905 g / cm³.

[0041] LDPEs may, in particular, have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm³.

[0042] VLDPEs can in particular have a density ranging from 0.905 (exclusive limit) to 0.915 g / cm3.

[0043] LLDPEs can in particular have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm3.

[0044] MDPEs can in particular have a density ranging from 0.926 to 0.940 g / cm3.

[0045] Linear HDPE polyethylenes (“High Density Polyethylene”) can be oriented polyethylenes such as, for example, MDOPE: “Machine Direction Oriented Polyethylene”) or BOPE: “biaxially oriented Polyethylene”).

[0046] There are also commercial polyethylenes, such as for example: LDPE FT5230 available from BOREALIS; LLDPE Dowlex 2045G available from DOW; HDPE 35060E available from DOW.

[0047] Polypropylene can be chosen from oriented polypropylene (OPP: “Oriented PolyPropylene”), bi-oriented polypropylene (BOPP: “Bi-axially Oriented Poly-Propylene”), cast polypropylene (cPP: “Cast PolyPropylene”).

[0048] There are also commercial polypropylenes, such as for example RC2472 available from HMC Polymers; RD226CF available from BOREALIS; ELTEX P available from INEOS.

[0049] The thickness of the Cl layer can vary from 10 to 120 pm, preferably from 20 to 100 pm.

[0050] The thickness of the C2 layer can vary from 10 to 120 pm, preferably from 20 to 100 pm.

[0051] Each of the Cl and C2 layers, independently of each other, may include one or more additives, for example chosen from the group consisting of sliding agents, pigments, inks, fillers, thermal stabilizers, UV stabilizers, antistatic agents, and mixtures thereof.

[0052] Preferably, each of the Cl and C2 layers, independently of each other, comprises more than 90% by weight of a polyolefin (or a mixture of polyolefins), more preferably more than 95% by weight, and even more preferably more than 99% by weight of a polyolefin (or a mixture of polyolefins) relative to the total weight of said Cl (or C2) layer respectively.

[0053] The two layers Cl and C2 mentioned above are preferably linked together by the adhesive layer.

[0054] Each of the Cl and C2 layers, independently of each other, may comprise at least one layer selected from aluminium oxides (AlOx), silicon oxides (SiOx), a metallisation layer, and mixtures thereof.

[0055] The metallization layer is well known in the field, and corresponds to a very thin layer of aluminum, typically having a thickness of less than 100 nm, preferably ranging from 3 to 60 nm. The layer can be conventionally made by vapor phase deposition on the surface of the substrate (of the Cl and / or C2 layer).

[0056] The AIOx and SiOx layers are typically less than 500 nm, preferably less than 200 nm, for example in the range of 5 to 150 nm.

[0057] If they are present on the Cl and / or C2 layers, these layers (AIOx, SiOx or metallization) can be in direct contact with the adhesive layer.

[0058] According to a preferred embodiment, the multilayer system Fl is such that: - Layer C1 comprises at least one polyethylene and layer C2 comprises at least one polyethylene, - one of the Cl or C2 layers comprises at least one polypropylene, and the other layer comprises at least one polyethylene, - layer C2 comprises at least one polypropylene and layer C2 comprises at least one polypropylene.

[0059] Even more preferably, layer C1 comprises at least one polyethylene and layer C2 comprises at least one polyethylene. The physicochemical characteristics of the polyethylenes in each of layers C1 and C2 may be identical or different.

[0060] Among the physico-chemical characteristics, we mean, for example, density, orientation, melting point, melt flow index (MFI: "Melt Flow Index"), tensile strength, turbidity...

[0061] Preferably, layer Cl comprises an MDOPE: "Machine Direction Oriented Polyethylene"), and layer C2 comprises an LDPE. Adhesive layer A / Adhesive composition CA

[0062] The adhesive layer A can have a thickness ranging from 1.2 to 5 pm.

[0063] The adhesive layer A is preferably obtained from the adhesive composition CA comprising an -OH component and an -NCO component such as:

[0064] - the -OH component is a composition comprising at least one Al polyol;

[0065]

[0066]

[0067] - the -NCO component is a composition comprising at least one polyurethane obtained by polyaddition reaction from a G2 composition comprising at least one polyisocyanate, and a G1 composition comprising at least one A2 polyol, said adhesive composition CA being characterized in that at least one of the polyols Al or A2 is selected from the following polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), and mixtures thereof: [Chem.l]

[0068] (I)

[0069] (II) (III-l)

[0070] (III-2) R* ;.R*

[0071] (III-3) (iv-1)

[0072]

[0073]

[0074] (IV-2) (IV-3) (V)

[0075]

[0076] (VI) in which: R° is a hydrogen, an ethyl or a methyl; R1 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R1 possibly comprising one or more heteroatoms selected from oxygen and sulfur; R2 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R2 possibly comprising one or more heteroatoms selected from oxygen and sulfur; Ra is an alkyl radical, saturated or unsaturated, preferably linear, comprising from 5 to 14 carbon atoms; Rb is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; x is an integer representing 0 or 1; y is an integer representing 0 or 1 z is an integer ranging from 1 to 9; s is an integer ranging from 0 to 6; t is an integer ranging from 1 to 4; f is an integer equal to 2 or 3; f' is an integer equal to 2 or 3; f and g are integers such that the number molecular mass (Mn) of the compound of formula (I) ranges from 600 to 20,000 g / mol; f' and g' are integers such that the number molecular mass (Mn) of the compound of formula (II) ranges from 600 to 20,000 g / mol; R3 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; R4 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R5 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R6 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; Each carbon-carbon bond, denoted by , represents either a single bond or a double bond. each bond means that the bond is geometrically oriented to one side or the other with respect to the double bond (cis (Z) or trans (E)); n1 is an integer such that the number molecular mass (Mn) of the compound of formula (III-1) ranges from 1000 to 20,000 g / mol; n2 is an integer such that the number molecular mass (Mn) of the compound of formula (III-2) ranges from 1000 to 20,000 g / mol; n3 is an integer such that the number molecular mass (Mn) of the compound of formula (III-3) ranges from 1000 to 20,000 g / mol; m1 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-1) ranges from 1000 to 20,000 g / mol; m2 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-2) ranges from 1000 to 20,000 g / mol; m3 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-3) ranges from 1000 to 20,000 g / mol; - p is an integer such that the number molecular mass (Mn) of the compound of formula (V) ranges from 1000 to 20,000 g / mol; - u is an integer such that the number molecular mass (Mn) of the compound of formula (VI) ranges from 1,000 to 20,000 g / mol; - Rc is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rd is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms;

[0077] or Rc and Rd together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles being optionally substituted by one or more saturated or unsaturated alkyl groups; - Re is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rf is a saturated linear alkyl radical comprising 6 to 8 carbon atoms; - Rg is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rh is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms;

[0078] or Rg and Rh together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles being optionally substituted by one or more saturated or unsaturated alkyl groups; - R' is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Ri is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms. - Rk is a saturated linear alkyl radical, comprising 6 to 10 carbon atoms. At least one of the polyols Al or A2 is chosen from the polyols of (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI). So : - only the Al polyol is chosen from among the polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI); or - only polyol A2 is chosen from among the polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI); or - the two polyols Al and A2 are chosen from the polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), the polyols Al and A2 being able to be identical or different.

[0080] Preferably, only polyol A2 is chosen from among the polyols of formulas (I), (II), (III-l), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI).

[0081] Preferably, in the aforementioned formula (I), R1 is a divalent or trivalent aliphatic radical, saturated or unsaturated, comprising from 2 to 60 carbon atoms. Even more preferably, R1 is an alkylene radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms, or even more advantageously, from 2 to 20 carbon atoms.

[0082] Preferably, in the aforementioned formula (I), R1 does not include heteroatoms.

[0083] Preferably, in the aforementioned formula (II), R2 is a divalent or trivalent aliphatic radical, saturated or unsaturated, comprising from 2 to 60 carbon atoms. Even more preferably, R2 is an alkylene radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms, or even more advantageously, from 2 to 20 carbon atoms.

[0084] Preferably, in the aforementioned formula (II), R2 does not include heteroatoms.

[0085] Preferably, in the aforementioned formula (V), R5 is a divalent aliphatic radical, saturated or unsaturated, comprising from 2 to 38 atoms.

[0086] Preferably, in the aforementioned formula (VI), R6 is a divalent aliphatic radical, saturated or unsaturated, comprising from 2 to 40 atoms.

[0087] In the context of the invention, a "saturated radical" is understood to mean a radical that does not contain a double bond. Conversely, an "unsaturated radical" is a radical containing one or more unsaturations.

[0088] In the context of the invention, "alkyl" means a linear or branched hydrocarbon radical.

[0089] In the context of the invention, an "aliphatic radical" may be linear, branched, or cyclic. Preferably, an "aliphatic radical" is a linear or branched radical.

[0090] Each carbon-carbon bond shown represents a single or double bond, in accordance with the valence rules of organic chemistry. COMPONENT -NCO Composition G1

[0091] Preferably, composition G1 comprises at least one polyol A2 selected from polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI) as defined above, and mixtures thereof.

[0092] Composition G1 may comprise a polyol A2 or a mixture of polyols A2. The mixture of polyols A2 may be a mixture of polyols of formula (I), a mixture of polyols of formula (II), a mixture of polyols of formula (III-1), a mixture of polyols of formula (III-2), a mixture of polyols of formula (III-3), a mixture of polyols of formula (IV-1), a mixture of polyols of formula (IV-2), a mixture of polyols of formula (IV-3), a mixture of polyols of formula (V), a mixture of polyols of formula (VI), or a mixture of polyols of different formulas (for example, a mixture of a polyol of formula (I) with a polyol of formula (II)). Polyols of formula (I)

[0093] Polyols of formula (I) can be obtained by polycondensation reaction between at least one compound of formula (VII) or one of its ester derivatives, poly(hydroxyalkanoate) derivatives or (macro)lactone derivatives, and at least one compound of formula (VIII):

[0094] [Chem.2] O Ra (VII)

[0095] [Chem.3] HO—iR1 h

[0096] (VIII)

[0097] in which R1, Ra, x, y, z, f, and .jX are such as defined previously for formula (I).

[0098] The polycondensation reaction can be carried out by any means known to those skilled in the art, for example in the presence of enzymes, esterification catalysts and / or transesterification catalysts known in the field. Preferably, the catalyst is chosen from the group consisting of sodium methoxide, magnesium oxide, zinc acetate, germanium dioxide, titanium tetraalkoxide (such as, for example, titanium tetrabutoxide), and mixtures thereof.

[0099] The polycondensation reaction can be carried out at a temperature ranging from 150°C to 260°C, preferably from 170°C to 240°C, possibly under reduced pressure, for example at about 10 mbar.

[0100] The reaction may optionally be carried out by mixing the different ingredients in "one-pot" or may be carried out in two separate steps: for example by a first oligomerization reaction of the compound of formula (VII) (or one of its aforementioned derivatives) in which the acid or ester function of a molecule is respectively esterified or transesterified with the -OH function carried by the carbon of another molecule of the same compound, followed by a second reaction in the presence of the compound of formula (VIII).

[0101] The compound of formula (VIII) may be a diol or a triol.

[0102] The compound of formula (VII) is preferably chosen from the group consisting of ethylene glycol (CAS: 107-21-1), diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, 1,6-hexanediol, 1,5-heptanediol, 1,7-heptanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-undecanediol, 3-ethyl-2-methyl-1,5-pentanediol, 2-ethyl-3-propyl-1,5-pentanediol, 2,4-Dimethyl-3-ethyl-1,5-pentanediol, 2-ethyl-4-methyl-3-propyl-1,5-pentadiol, 2,3-Diethyl-4-methyl-1,5-pentanediol, 3-Ethyl-2,2,4-trimethyl-1,5-pentadiol, 2,2-Dimethyl-4-ethyl-3-propyl-1,5-pentanediol, 2-Methyl-2-propyl-1,5-pentanediol, 2,4-Dimethyl-3-ethyl-2-propyl-1,5-pentanediol, 2,3-Dipropyl-4-ethyl-2-methyl-1,5-pentanediol, 2-Butyl-2-ethyl-1,5-pentanediol, 2-Butyl-2,3-Diethyl-4-methyl-1,5-pentanediol, 2-butyl-2,4-diethyl-3-propyl-1,5-pentanediol,3-Butyl-2-propyl-1,5-pentanediol, 2-methyl-1,5-pentanediol (CAS: 42856-62-2), 3-methyl-1,5-pentanediol (MPD, CAS: 4457-71-0), 2,2-dimethyl-1,3-pentanediol (CAS: 2157-31-5), 2,2-dimethyl-1,5-pentanediol (CAS: 3121-82-2), 3,3-dimethyl-1,5-pentanediol (CAS: 53120-74-4), 2,3-dimethyl-1,5-pentanediol (CAS: 81554-20-3), 2,2-dimethyl-1,3-propanediol (Neopentyl glycol - NPG, CAS: 126-30-7), 2,2-diethyl-1,3-propanediol (CAS: 115-76-4), 2-methyl-2-propyl-1,3-propanediol (CAS: 78-26-2), 2-butyl-2-ethyl-1,3-propanediol (CAS: 115-84-4), 2-methyl-1,3-propanediol (CAS: 2163-42-0), 2-benzyloxy-1,3-propanediol (CAS: 14690-00-7), 2,2-dibutyl-1,3-propanediol (CAS: 24765-57-9), 2,2-diisobutyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, , 2-Ethyl-1,6-Hexanediol (CAS: 15208-19-2), 2,5-Dimethyl-1,6-Hexanediol (CAS: 49623-11-2), 5-Methyl-2-(l-Methylethyl)-l,3-Hexanediol (CAS: 80220-07-1), 1,4-Dimethyl-1,4-Butanediol, 1,5-Hexanediol (CAS: 928-40-5), 3-Methyl-1,6-Hexanediol (CAS: 4089-71-8), 3-Tert-Butyl-1,6-Hexanediol (CAS: 82111-97-5), 1,3-Heptanediol (CAS: 23433-04-7), 1,2-Octanediol (CAS: 23433-04-7), 1,2-Octanediol (CAS: 23433-04-7), 1,2-Octanediol (CAS: 23433-04-7), 1,3-Hept ... : 1117-86-8), 1,3-octanediol (CAS: 23433-05-8), 2,2,7,7-tetramethyl-1,8-octanediol (CAS: 27143-31-3), 2-methyl-1,8-octanediol (CAS: 109359-36-6), 2,6-dimethyl-1,8-octanediol (CAS: 75656-41-6), 1,7-octanediol (CAS: 3207-95-2), 4,4,5,5-tetramethyl-3,6-dioxa-1,8-octanediol (CAS: 76779-60-7), 2,2,8,8-tetramethyl-1,9-nonanediol (CAS: 85018-58-2), 1,2-nonanediol (CAS: 42789-13-9), 2,8-dimethyl-1,9-nonanediol (CAS: 40326-00-9), 1,5-nonanediol (CAS: 13686-96-9), 2,9-dimethyl-2,9-dipropyl-1,10-decanediol (CAS: 85018-64-0), 2,9-Dibutyl-2,9-dimethyl-1,10-decanediol (CAS: 85018-65-1), 2,9-dimethyl-2,9-dipropyl-1,10-decanediol (CAS: 85018-64-0), 2,9-diethyl-2,9-dimethyl-1,10-decanediol (CAS: 85018-63-9), 2,2,9,9-tetramethyl-1,10-decanediol (CAS: 35449-36-6), 2-nonyl-1,10-decanediol (CAS: 48074-20-0), 1,9-decanediol (CAS: 128705-94-2), 2,2,6,6,10,10-hexamethyl-4,8-dioxa-l,ll-undecanediol (CAS: 112548-49-9), l-phenyl-l,ll-undecanediol (CAS: 109217-58-5), 2-octyl-l,ll-undecanediol (CAS: 48074-21-1), 2,10-diethyl-2,10-dimethyl-l,ll-undecanediol (CAS: 85018-66-2), 2,2,10,10-tetramethyl-l,ll-undecanediol (CAS: 35449-37-7), l-phenyl-l,ll-undecanediol (CAS: 109217-58-5), 1,2-undecanediol (CAS: 13006-29-6), 1,2-dodecanediol (CAS: 1119-87-5), 2,11-dodecanediol (CAS: 33666-71-6), 2,1-diethyl-2,1-dimethyl-1,12-dodecanediol (CAS: 85018-68-4), 2,1-dimethyl-2,1-dipropyl-1,12-dodecanediol (CAS: 85018-69-5), 2,1-dibutyl-2,1-dimethyl-1,12-dodecanediol (CAS: 85018-70-8), from, 2,2,11,1-tetramethyl-1,12-dodecanediol (CAS: 5658-47-9), 1,11-dodecanediol (CAS: 80158-99-2), 11-methyl-1,7-dodecanediol (CAS: 62870-49-9), 1,4-dodecanediol (CAS: 38146-95-1), 1,3-dodecanediol (CAS: 39516-24-0), 1,10-dodecanediol (CAS: 39516-27-3), 2,11-dimethyl-2,11-dodecanediol (CAS: 22092-59-7), 1,5-dodecanediol (CAS: 20999-41-1), 6,7-dodecanediol (CAS: 91635-53-9), 1,9-octadecandiol (CAS: 3155-35-9), 1,12-octadecanediol (CAS: 2726-73-0), a dimeric and / or trimer fatty alcohol, cyclohexanedimethanol, hydrogenated bisphenol A, cyclohexanediol, glycerol, trimethylolpropane, 1,2,6-hexanetriol, ricinoleic alcohol, and mixtures thereof.

[0103] In the context of the invention, and unless otherwise stated, the terms "fatty alcohol dimer", "dimer fatty alcohol" and "dimerized fatty alcohol" are understood to be equivalent.

[0104] The term “dimeric fatty alcohol” covers both saturated and unsaturated dimeric fatty alcohols.

[0105] Dimeric fatty alcohols can typically be obtained, in the form of a composition, respectively by reduction with, for example, LiAlH4 or by catalytic hydrogenation of dimeric fatty acids (and / or their ester derivatives), said dimeric fatty acids preferably comprising 20 to 40 carbon atoms. Such a process is, for example, described in DE 1,768,313.

[0106] Hydrogenation can be carried out in such a way as to retain all or part of the double bonds, which advantageously leads to unsaturated dimeric fatty alcohols.

[0107] Dimeric fatty alcohols can also be obtained by dimerization of unsaturated fatty alcohols with basic alkaline earth metal compounds, as for example described in DE 1,198,348, or by dimerization of unsaturated fatty alcohols in presence of silica / alumina catalysts and basic alkali compounds such as for example described in WO 91 / 13918.

[0108] Certain dimeric fatty alcohols (CAS: 147853-32-5) are also commercially available. For example, a composition of fatty alcohol dimers comprising 20 to 40 carbon atoms with an IOH between 202 and 212 mg KOH / g (M between 529 and 556 g) is marketed under the names PRIPOL® 2030 and PRIPOL® 2033 by CRODA, RADIANOL® 1990 and RADIANOL® 1991 by OLEON, and SOVERMOL® 908 by COGNIS.

[0109] The term "trimeric fatty alcohol" covers saturated and unsaturated trimer fatty alcohols.

[0110] Trimeric fatty alcohols can typically be obtained, in the form of a composition, respectively by reduction or hydrogenation of trimeric fatty acids (and / or their ester derivatives), said trimeric fatty acids preferably comprising 30 to 60 carbon atoms.

[0111] The processes mentioned above for dimeric fatty alcohols also apply to trimer fatty alcohols.

[0112] Even more preferably, the compound of formula (VIII) is a diol, preferably chosen from propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, ricinoleic alcohol, 9-hydroxystearic alcohol, 10-hydroxystearic alcohol, 12-hydroxystearic alcohol, 9-hydroxymethylstearic alcohol and 10-hydroxymethylstearic alcohol, even more preferably the compound of formula (VIII) being propylene glycol.

[0113] The compound of formula (VII) can be obtained by saponification of the triglyceride precursor.

[0114] The compound of formula (VII) is preferably selected from the group consisting of ricinoleic acid (CAS: 141-22-0), isoricinoleic acid (CAS: 73891-08-4), strophantic acid (CAS: 38231-95-7), densipolic acid (CAS: 7121-47-3), lesquerolic acid (CAS: 4103-20-2), auricolic acid (CAS: 37780-50-0), 12-hydroxystearic acid (CAS: 106-14-9), 9-hydroxymethylstearic acid, 10-hydroxymethylstearic acid, and mixtures thereof.

[0115] The ester derivatives of the compound of formula (VII) above are preferably selected from ricinoleic acid esters, isoricinoleic acid esters, densipolic acid esters, lesquerolic acid esters, strophanturic acid esters, auricolic acid esters, 12-hydroxystearic acid esters, 9-hydroxymethylstearic acid esters, 10-hydroxymethylstearic acid esters, and mixtures thereof.

[0116] Ester derivatives of compounds of formula (VII) are even more preferentially selected from methyl ricinoleate, ethyl ricinoleate, methyl isoricinoleate, ethyl isoricinoleate, methyl strophanturate, ethyl strophanturate, methyl lesquerolate, ethyl lesquerolate, methyl densipolate, ethyl densipolate, methyl auricolate, ethyl auricolate, methyl 12-hydroxy stearate, ethyl 12-hydroxy stearate, ethyl 9-hydroxymethyl stearate, ethyl 9-hydroxymethyl stearate, ethyl 10-hydroxymethyl stearate, ethyl 10-hydroxymethyl stearate, and mixtures thereof.

[0117] Ester derivatives of the compound of formula (VII) can be obtained by methanolysis or ethanolysis of the triglyceride precursor.

[0118] The poly(hydroxyalkanoate) derivatives of the compounds of formula (VII) may be selected from: methyl poly(ricinoleate), ethyl poly(ricinoleate), methyl poly(isoricinoleate), ethyl poly(isoricinoleate), methyl poly(strophanturate), ethyl poly(strophanturate), methyl poly(lesquerolate), ethyl poly(lesquerolate), methyl poly(densipolate), ethyl poly(densipolate), methyl poly(auricolate), ethyl poly(auricolate), methyl poly(12-hydroxystearate), ethyl poly(12-hydroxystearate), methyl poly(9-hydroxymethylstearate, ethyl poly(9-hydroxymethylstearate), methyl poly(10-hydroxymethylstearate), ethyl poly(10-hydroxymethylstearate) and mixtures thereof.

[0119] (Macro)lactone derivatives of compounds of formula (VII) include lactone derivatives and macrolactone derivatives.

[0120] The lactone derivatives may be selected from the group consisting of delta-decalactone, gamma-decalactone, delta-undecalactone, gamma-undecalactone, delta-dodecalactone, gamma-dodecalactone, delta-tetralactone, gamma-tetralactone, delta-hexadecalactone, gamma-hexadecalactone, delta-octadecalactone, gamma-octadecalactone, delta-pentalactone, gamma-pentalactone, ricinoleic lactone and mixtures thereof.

[0121] The (macro)lactone derivatives of the compounds of formula (VII) can be obtained by oligomerization / cyclization at a temperature greater than or equal to 130°C of a composition comprising a compound of formula (VII) above.

[0122] A process is for example described in "Macrolactones and Polyesters from ri-cinoleic acid", Biomacromolecules 2005, 6, 1679-1688.

[0123] Preferably, the polyol of formula (I) is obtained by polycondensation reaction between at least ricinoleic acid or one of its ester derivatives such as, for example, methyl ricinoleate or (macro)lactone ricinoleate, and at least one compound of formula (VIII).

[0124] Polyols of formula (I) are preferably those of formula (LA) or (LB) following:

[0125] [Chem.4] (AI)

[0126] with x, y, z, g, Ra, R1, and being such as defined previously for formula (II).

[0127] Preferably, in the above-mentioned formulas (I) and (VII), Ra represents a linear alkyl radical, saturated or unsaturated, comprising 6 to 9 carbon atoms.

[0128] Preferably, in the above-mentioned formulas (I) and (VII), x represents 1, y represents 0, and z is an integer from 6 to 9, preferably z representing 7.

[0129] Polyols of formula (I) are preferably those of formula (IA). Polyols of formula (LA) are polyols of formula (I) in which f = 2.

[0130] In polyols of formula (I), (IA), and (IB), x, y, z, and Ra, independently of each other, may be identical or different for each repeating unit g. For example, in one repeating unit g, x = 0, and in another repeating unit g, x = 1. This may, in particular, result from the use of mixtures of ingredients to form the polyol of formula (I), (IA), or (IB). This is also true for each repeating unit g on either side of the radical R1.

[0131] In addition, the number g of repeating units on either side of the radical R1 can be identical or different, preferably identical.

[0132] Even more preferably, polyols of formula (I) are polyols of formula (LA-1) or (LA-2):

[0133] [Chem.5]

[0134] (IAl)

[0135] (IA-2)

[0136] in which R1, x, y, z, g, and are such as defined above, v is an integer representing 0 or 1, and w is an integer from 0 to 10, preferably from 0 to 5, the polyols of formula (I) being more preferably polyols of formula (IAl).

[0137] Preferably, in formulas (I), (IA), (IA1) and (IA-2): - g is an integer such that the number molecular mass (Mn) of the compound of formula (I), (IA), (IAl) or (IA-2) ranges from 600 to 20,000 g / mol; - R1 is an alkylene radical, saturated or unsaturated, linear or branched, comprising from 2 to 18 carbon atoms, preferably from 2 to 12 carbon atoms and even more preferably from 2 to 6 carbon atoms.

[0138] The polyol of formula (I) is preferably the following:

[0139] [Chem.6]

[0140] in which g and R1 are as defined above, R1 preferably being a branched propylene. Polyols of formula (II)

[0141] Polyols of formula (II) can be obtained by a process comprising: - i) a polycondensation reaction between at least one compound of formula (VII) or one of its ester derivatives, poly(hydroxyalkanoate) derivatives or (macro)lactone derivatives, as described above, with at least one compound of formula (IX) or one of its ester derivatives:

[0142] [Chem.7] I hqqc— ......(IX)

[0143] in which f' and R2 are such as defined previously in formula (II);

[0144] then - ii) an alkoxylation reaction of the product obtained in step i) with a compound of formula (X):

[0145] [Chem.8] A ^R® (X)

[0146] in which R° is such as defined previously in formula (II).

[0147] The definition, embodiments, and preferred embodiments for the compound of formula (VII), as well as its derivatives, are identical to those described previously, and are not repeated. They are also applicable for the preparation of polyols of formula (II).

[0148] The compound of formula (IX) may be a dicarboxylic acid or a carboxylic triacid, preferably a dicarboxylic acid.

[0149] The compound of formula (IX) may be selected from the group consisting of propanedioic acid (C3), butanedioic acid (C4), pentanedioic acid (C5), hexanedioic acid (C6), heptanedioic acid (C7), octanedioic acid (C8), nonanedioic acid (C9), decanedioic acid (C10), undecanedioic acid (C11), dodecanedioic acid (C12), tridecanedioic acid (C13), tetradecanedioic acid (C14), pentadecanedioic acid (C15), hexadecanedioic acid (C16), heptadecanedioic acid (C17), octadecanedioic acid (C18), acid nonadecanedioic acid (C19), eicosa-nedioic acid (C20), heneicosanedioic acid (C21), dimeric fatty acids (C21), docosanedioic acid (C22), trocosanedioic acid (C23), tetra-cosanedioic acid (C24), pentacosanedioic acid (C25), hexacosa-nedioic acid (C26), heptacosanedioic acid (C27),of octacosanedioic acid (C28), nonacosanedioic acid (C29), triacontanedioic acid (C30), cyclohexanediacetic acid (C10), 1,4-cyclohexanedicarboxylic acid (C8), 3,4,5,6-tetrahydrophthalic acid (C8) and their unsaturated and / or branched analogues, 2,5-furanedicarboxylic acid (C6), isophthalic acid (C8), terephthalic acid (C8), dimeric fatty acids (C8), dimeric fatty acids (C20), dimeric fatty acids (C21), dimeric fatty acids (C22), dimeric fatty acids (C26), dimeric fatty acids (C36), 1,2,3-propanetricarboxylic acid (C6), acid 1,3,5-cyclohexanetricarboxylic acid (C9), 1,3,5-benzenetricarboxylic acid (C9), trimellitic acid (C9), trimer fatty acids (C54), their unsaturated and / or branched analogues, and mixtures thereof.

[0150] In the context of the invention, the terms "dimeric fatty acid", "dimerized fatty acid" and "fatty acid dimer" are understood to be equivalent.

[0151] C21 fatty acid dimers, and their ester derivatives, can be prepared by an energizing reaction between acrylic acid and linoleic acid (Cl8:2) or their ester derivatives. One such process is described in US 5,053,534.

[0152] Examples of C21 dimeric fatty acids are:

[0153] [Chem.9]

[0154] C22 fatty acid dimers, and their ester derivatives, can be prepared by pyrolysis of castor oil. A preparation process is described in particular in Yasa, SR et al. “Synthesis of 10-undecenoic acid based C22-dimer acid esters and their evaluation as potential lubricant basestocks”, published in “Industrial Crops & Products”, 2017, 103, 141-151, Elsevier Edition

[0155] [Chem. 10] O UNHCR ......... ....... A Y .-x,- ...... ...... , has

[0156] C18-C22 fatty acid dimers, and their ester derivatives, can be prepared by self-metathesis of undecylenic acid, oleic acid, ricinoleic acid, and 11-eicosenoic acid. A preparation process is described in particular in Ngo, HL et al. in “Metathesis of Unsaturated Fatty Acids: Synthesis of Long Chain Unsaturated-α,α-Dicarboxylic Acids”, published in JAOCS J. of Am. Org. Chem. Soc. 2006, 83 (7), 629-634.

[0157] [Chem. 11] A x. ,.-x .-x xx -X -X Xx "X 4>H ho^ 'xx Y" Q HO. ..-X x -X xX -x V X-- XX" XX vx X XX XX' XX XX VH

[0158] C36 fatty acid dimers, and their ester derivatives, can be prepared by oligomerization of mono- and polyunsaturated fatty acids or their ester derivatives. A preparation process is described in particular in WO 01 / 09066.

[0159] Examples of C36 fatty acid dimers are:

[0160] [Chem. 12]

[0161] There are also commercially available dimeric fatty acids. Examples of unsaturated dimeric fatty acids include PRIPOL 1012 (mixture of 97% minimum by weight of dimer / 1% maximum by weight of trimer), PRIPOL 1013 (mixture of 95 to 98% by weight of dimer / 2 to 4% by weight of trimer), PRIPOL 1017 (mixture of 75 to 80% by weight of dimer / 20 to 23% by weight of trimer), PRIPOL 1022 (mixture of 72 to 79% dimer / 20 to 23% trimer), and PRIPOL (mixture of 75 to 80% by weight of dimer / 18 to 22% by weight of trimer), marketed by CRODA, as well as RADIACID 0970 (mixture of 95 to 98% by weight of dimer / 3% maximum by weight of trimer). of trimer) marketed by OLEON, or as an example of hydrogenated dimeric fatty acids PRIPOL 1006 (mixture 92 to 98% by weight of dimer / 1% max. by weight of trimer) and PRIPOL 1025 (mixture 75 to 80% by weight of dimer / 18 to 22% by weight of trimer) marketed by CRODA.

[0162] Trimeric fatty acids are also commercially available. PRIPOL 1040 is an example of an unsaturated trimeric fatty acid. (mixture containing 75% by weight of trimer) marketed by CRODA or RADIACID 0980 (mixture containing 50 to 90% of trimer) marketed by OLEON.

[0163] Trimeric fatty acids and ester derivatives of trimeric fatty acids are typically by-products obtained during fatty acid dimerization. Trimeric fatty acids and ester derivatives of trimeric fatty acids can also be isolated and purified, for example by distillation.

[0164] Preferably, the compound of formula (IX) is chosen, the group consisting of propanedioic acid (C3), butanedioic acid (C4), pentanedioic acid (C5), hexanedioic acid (C6), heptanedioic acid (C7), octanedioic acid (C8), nonanedioic acid (C9), decanedioic acid (C10), undecanedioic acid (C11), dodecanedioic acid (C12), tridecanedioic acid (C13), tetradecanedioic acid (C14), pentadecanedioic acid (C15), hexadecanedioic acid (C16), heptadecanedioic acid (C17), octadecanedioic acid (C18), acid nonadecanedioic acid (C19), eicosa-nedioic acid (C20), heneicosanedioic acid (C21), docosanedioic acid (C22), trocosanedioic acid (C23), tetracosanedioic acid (C24), pentacosanedioic acid (C25), hexacosanedioic acid (C26), hep-tacosanedioic acid (C27), octacosanedioic acid (C28),of nonacosa-nedioic acid (C29), triacontanedioic acid (C30), their unsaturated and / or branched analogues, and mixtures thereof.

[0165] Reaction i) can be carried out by any means known to those skilled in the art, for example in the presence of enzymes, esterification catalysts or transesterification catalysts known in the field. Preferably, the catalyst is chosen from the group consisting of sodium methoxide, magnesium oxide, zinc acetate, titanium tetraalkoxide (such as, for example, titanium tetrabutoxide), and mixtures thereof.

[0166] Reaction i) can be carried out at a temperature ranging from 150 to 260°C, preferably from 170°C to 240°C, possibly under reduced pressure, for example at about 10 mbar.

[0167] Reaction i) advantageously leads to a composition comprising at least one polyol of the following formulas (ILA) or (ILB):

[0168] [Chem. 13] (HE HAS)

[0169] in which R2, Ra, x, y, z, g', and being such as defined previously for formula (II).

[0170] The compound of formula (IX) may be selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and mixtures thereof.

[0171] Reaction ii) can be carried out at a temperature ranging from 70 to 150°C, preferably from 80°C to 130°C, and advantageously under 1 to 10 bars of pressure.

[0172] Polyols of formula (II) are preferably those of formula (ILA). Polyols of formula (ILA) are polyols of formula (II) in which f = 2.

[0173] In polyols of formula (II), (ILA), and (ILB): x, y, z, and Ra, independently of each other, may be identical or different for each repeating unit g'. For example, in one repeating unit g', x = 0, and in another repeating unit g', x = 1. This may, in particular, result from the use of mixtures of ingredients to form the polyol of formula (II), (ILA), or (ILB). This is also true for each repeating unit g' on either side of the radical R2.

[0174] In addition, the number g' of repeating units on either side of the radical R2 can be identical or different, preferably identical.

[0175] Similarly, R° is identical or different for each repeating unit t, and this also on both sides of the radical R2.

[0176] Preferably, the polyols of formula (II) are polyols of formula (ILA-1) or (ILA-2):

[0177] [Chem. 14]

[0178] (ILA-1)

[0179] (II-A-2)

[0180] in which R°, R2, x, y, z, g', t and are such as defined above, v is an integer representing 0 or 1, and w is an integer from 0 to 10, preferably from 0 to 5.

[0181] Preferably, in formulas (II), (II-A), (II-A-1) and (II-A-2): - g' is an integer such that the number molecular mass (Mn) of the compound of formula (II), (II-A), (II-A-1) or (II-A-2) ranges from 600 to 20,000 g / mol; - R° is a methyl or ethyl; - R2 is an alkylene radical, saturated or unsaturated, comprising from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms and even more preferably from 2 to 6 carbon atoms.

[0182] The polyol of formula (II) is preferably the following:

[0183] [Chem. 15]

[0184] in which R°, t, R2 and g' are such as defined previously. Polyols of formula (III-l), (III-2) and (III-3)

[0185] The polyols of formula (III-1) above can be obtained by polycondensation reaction of at least one fatty acid dimer of formula (XL1), or one of its ester derivatives, with a diol of formula (XII):

[0186] [Chem. 16]

[0187] (XI-1)

[0188] in which Rc, Rd, and are such as defined previously for formula (iii-D;

[0189] [Chem 17]

[0190] OH-R3-OH

[0191] (XII)

[0192] in which R3 is as defined previously for formula (III-1).

[0193] The polyol of formula (III-2) mentioned above can be obtained by polycondensation reaction of at least one fatty acid dimer of formula (XL2), or one of its ester derivatives, with a diol of formula (XII):

[0194] [Chem. 18] <>y A .... ... / V MC - VW y

[0195] (X-2)

[0196] [Chem. 19] OH-R3-OH (XH)

[0197] in which R3 and Re are as defined previously.

[0198] The polyol of formula (III-3) mentioned above can be obtained by polycondensation reaction of at least one fatty acid dimer of formula (XL3), or one of its ester derivatives, with a diol of formula (XII):

[0199] [Chem.20] RF (XI-3)

[0200] [Chem.21] OH-A-GH (XH)

[0201] in which R3 and Rf are as defined above.

[0202] The polycondensation reaction can be carried out at a temperature ranging from 150°C to 260°C, preferably from 170°C to 240°C, possibly under reduced pressure, for example at about 10 mbar.

[0203] The polycondensation reaction can be carried out in the presence of an esterification catalyst under typical conditions.

[0204] The diol of formula (XII) may be selected from the group consisting of ethylene glycol (CAS: 107-21-1), diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, 1,6-hexanediol, 1,5-heptanediol, 1,7-heptanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,9-Octadecanediol (CAS: 3155-35-9), 1,12-Octadecanediol, 3-Ethyl-2-methyl-1,5-pentanediol, 2-Ethyl-3-propyl-1,5-pentanediol, 2,4-Dimethyl-3-ethyl-1,5-pentanediol, 2-ethyl-4-methyl-3-propyl-1,5-pentadiol, 2,3-diethyl-4-methyl-1,5-pentanediol, 3-ethyl-2,2,4-trimethyl-1,5-pentadiol, 2,2-dimethyl-4-ethyl-3-propyl-1,5-pentanediol, 2-methyl-2-propyl-1,5-pentanediol, 2,4-dimethyl-3-ethyl-2-propyl-1,5-pentanediol, 2,3-dipropyl-4-ethyl-2-methyl-1,5-pentanediol, 2-butyl-2-ethyl-1,5-pentanediol, 2-butyl-2,3-diethyl-4-methyl-1,5-pentanediol, 2-butyl-2,4-diethyl-3-propyl-1,5-pentanediol, 3-Butyl-2-propyl-1,5-pentanediol, 2-methyl-1,5-pentanediol (CAS: 42856-62-2), 3-methyl-1,5-pentanediol (MPD, CAS: 4457-71-0), 2,2-dimethyl-1,3-pentanediol (CAS: 2157-31-5), 2,2-dimethyl-1,5-pentanediol (CAS: 3121-82-2), 3,3-dimethyl-1,5-pentanediol (CAS: 53120-74-4), 2,3-dimethyl-1,5-pentanediol (CAS: 81554-20-3), 2,2-dimethyl-1,3-propanediol (Neopentyl glycol - NPG, CAS: 126-30-7), 2,2-diethyl-1,3-propanediol (CAS: 115-76-4), 2-methyl-2-propyl-1,3-propanediol (CAS: 78-26-2), 2-butyl-2-ethyl-1,3-Propanediol (CAS: 115-84-4), 2-Methyl-1,3-propanediol (CAS: 2163-42-0), 2-Benzyloxy-1,3-propanediol (CAS: 14690-00-7), 2,2-Dibutyl-1,3-propanediol (CAS: 24765-57-9), 2,2-Diisobutyl-1,3-propanediol, 2,4-Diethyl-1,5-pentanediol, 2-Ethyl-1,6-hexanediol (CAS: 15208-19-2), 2,5-Dimethyl-1,6-hexanediol (CAS: 49623-11-2), 5-Methyl-2-(1-methylethyl)-1,3-hexanediol (CAS: 80220-07-1), 1,4-dimethyl-1,4-butanediol, 1,5-hexanediol (CAS: 928-40-5), 3-methyl-1,6-hexanediol (CAS: 4089-71-8), 3-tert-butyl-1,6-hexanediol (CAS: 82111-97-5), 1,3-heptanediol (CAS: 23433-04-7), 1,2-octanediol (CAS: 1117-86-8), 1,3-octanediol (CAS: 23433-05-8), 2,2,7,7-tetramethyl-1,8-octanediol (CAS: 27143-31-3), 2-methyl-l,8-octanediol (CAS: 109359-36-6), 2,6-dimethyl-l,8-octanediol (CAS: 75656-41-6), 1,7-octanediol (CAS: 3207-95-2), 4,4,5,5-tetramethyl-3,6-dioxa-l,8-octanediol (CAS: 76779-60-7), 2,2,8,8-tetramethyl-l,9-Nonanediol (CAS: 85018-58-2), 1,2-nonanediol (CAS: 42789-13-9), 2,8-dimethyl-1,9-nonanediol (CAS: 40326-00-9), 1,5-nonanediol (CAS: 13686-96-9), 2,9-dimethyl-2,9-dipropyl-1,0-decanediol (CAS: 85018-64-0), 2,9-dibutyl-2,9-dimethyl-1,10-decanediol (CAS: 85018-65-1), 2,9-dimethyl-2,9-dipropyl-1,0-decanediol (CAS: 85018-64-0), 2,9-Diethyl-2,9-dimethyl-1,10-decanediol (CAS: 85018-63-9), 2,2,9,9-tetramethyl-1,10-decanediol (CAS: 35449-36-6), 2-nonyl-1,10-decanediol (CAS: 48074-20-0), 1,9-decanediol (CAS: 128705-94-2), 2,2,6,6,10,10-hexamethyl-4,8-dioxa-1,11-undecanediol (CAS: 112548-49-9), 1-phenyl-1,11-undecanediol (CAS: 109217-58-5), 2-octyl-1,11-undecanediol (CAS: 48074-21-1), 2,10-diethyl-2,10-dimethyl-1,11-undecanediol (CAS: 85018-66-2), 2,2,10,10-tetramethyl-1,11-undecanediol (CAS: 35449-37-7), , l-Phenyl-l,ll-undecanediol (CAS: 109217-58-5), 1,2-undecanediol (CAS: 13006-29-6), 1,2-dodecanediol (CAS: 1119-87-5), 2,11-dodecanediol (CAS: 33666-71-6), 2,ll-diethyl-2,ll-dimethyl-l,12-dodecanediol (CAS: 85018-68-4), 2,ll-dimethyl-2,ll-dipropyl-l,12-dodecanediol (CAS: 85018-69-5), 2,ll-dibutyl-2,ll-dimethyl-l,12-dodecanediol (CAS: 85018-70-8), 2,2,11,1-tetramethyl-1,12-dodecanediol (CAS: 5658-47-9), 1,11-dodecanediol (CAS: 80158-99-2), 11-methyl-1,7-dodecanediol (CAS: 62870-49-9), 1,4-dodecanediol (CAS: 38146-95-1), 1,3-dodecanediol (CAS: 39516-24-0), 1,10-dodecanediol (CAS: 39516-27-3), 2,11-dimethyl-2,11-dodecanediol (CAS: 22092-59-7), 1,5-dodecanediol (CAS: 20999-41-1), 6,7-dodecanediol (CAS: 91635-53-9), cyclohexanedimethanol, hydrogenated bisphenol A, cyclo-hexanediol, ricinoleic alcohol, and mixtures thereof.

[0205] Preferably, in formulas (III-1), (III-2), (III-3), (XII), R3 is a saturated alkylene radical comprising from 2 to 40 carbon atoms, preferably from 2 to 10 carbon atoms.

[0206] The fatty acid dimers and their methods of preparation are as detailed previously in this application.

[0207] The fatty acid dimer of formula (XL1) may be selected from those in which: - Rc is an unsaturated linear alkyl radical comprising 9 carbon atoms, and Rd is an unsaturated linear alkyl radical comprising 9 carbon atoms; - Rc and Rd together form an unsaturated ring or bicycle comprising 6 to 12 carbon atoms, substituted by one or more saturated or unsaturated alkyl groups, said alkyl groups comprising 5 to 8 carbon atoms; or - Rc and Rd together form an aromatic ring comprising 6 carbon atoms, substituted by one or more saturated alkyl groups, said alkyl groups comprising from 5 to 8 carbon atoms.

[0208] C36 fatty acid dimers of formula (XL1) are preferably selected from the group consisting of the dimers below and their mixtures advantageously obtained from a fatty acid cut containing oleic (C18:1), linoleic (Cl8:2) and linolenic (Cl8:3) acids:

[0209] [Chem.22]

[0210]

[0211] The C21 fatty acid dimers of formula (XL2) and (XL3) are preferably chosen from the group consisting of the dimers below and their mixtures, which can advantageously be obtained via a reaction between acrylic acid and linoleic acid (Cl8:2): [Chem. 23] HO

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] Polyols of formula (IV-1), (IV-2) and (IV-3) The polyols of formula (IV-1) mentioned above can be obtained by a polycondensation reaction of at least one dimeric fatty alcohol of formula (XIIL1) with a dicarboxylic acid of formula (XIV): [Chem. 24] (xm-i) [Chem. 25] Hoac-R <coüh (XIV). in which Rg, Rh, R4, and are such as defined previously for formula (IV-1). Polyols of formulas (IV-2) and (IV-3) can be obtained by a polycondensation reaction of at least one dimeric fatty alcohol of formulas (XL2) and (XL3) respectively, with a dicarboxylic acid of formula (XIV): [Chem.26] (xm-2) RJ

[0220] (XIII-3)

[0221] [Chem.27] HOOÇ-R^COOH. (XIV)

[0222] in which R4, R', and Rj are such as defined previously for formulas (IV-2) and (IV-3)

[0223] The polycondensation reaction can be carried out at a temperature ranging from 150 to 260°C, preferably from 170°C to 240°C, possibly under reduced pressure, for example at about 10 mbar.

[0224] The polycondensation reaction can be carried out in the presence of a catalyst under typical esterification conditions. These can be the same as those already mentioned previously for other polyol formulas.

[0225] The diacid of formula (XIV) is preferably selected from the group consisting of propanedioic acid (C3), butanedioic acid (C4), pentanedioic acid (C5), hexanedioic acid (C6), heptanedioic acid (C7), octanedioic acid (C8), nonanedioic acid (C9), decanedioic acid (C10), undecanedioic acid (C11), dodecanedioic acid (C12), tridecanedioic acid (C13), tetradecanedioic acid (C14), pentadecanedioic acid (C15), hexadecanedioic acid (C16), heptadecanedioic acid (C17), octadecanedioic acid (C18), acid nonadecanedioic acid (C19), eico-sanedioic acid (C20), heneicosanedioic acid (C21), docosanedioic acid (C22), trocosanedioic acid (C23), tetracosanedioic acid (C24), pentacosanedioic acid (C25), hexacosanedioic acid (C26), hep-tacosanedioic acid (C27), octacosanedioic acid (C28),of nonacosa-nedioic acid (C29), triacontanedioic acid (C30), and their unsaturated and branched analogues, and mixtures thereof.

[0226] C36 fatty alcohol dimers of formula (XIIL1) are preferably selected from the group consisting of the dimers below and mixtures thereof, which can advantageously be obtained according to the processes mentioned above in this application:

[0227] [Chem.28]

[0228] The C21 fatty alcohol dimers of formulas (XIII-2) and (XIIL3) are preferably chosen from the group consisting of the dimers below and their mixtures, which can advantageously be obtained by reduction or hydrogenation of the corresponding fatty acid dimers:

[0229]

[0230]

[0231]

[0232] Polyols of formula (V) Polyols of formula (V) can be obtained by polycondensation reaction of a diol of formula (XV) with a dicarboxylic acid of formula (XVI): [Chem.29]

[0233]

[0234] (XV) [Chem. 30] HOOC-R5-COOH (XVI) in which Rb, R5, x, y, z, and are such as defined previously. The polycondensation reaction can be carried out by any means known to those skilled in the art, for example, in the presence of enzymes or transesterification catalysts known in the field. Preferably, the catalyst is chosen from the group consisting of sodium methoxide, magnesium oxide, zinc acetate, and...

[0235]

[0236]

[0237]

[0238]

[0239] germanium dioxide, titanium tetraalkoxide (such as titanium tetrabutoxide), and mixtures thereof. The polycondensation reaction can be carried out at a temperature ranging from 150°C to 260°C, preferably from 170°C to 240°C, possibly under reduced pressure, for example at about 10 mbar. The diol of formula (XV) may be selected from: ricinoleic alcohol (CAS: 540-11-4), isoricinoleic alcohol (CAS: 100242-34-0), strophantic alcohol (CAS: 100242-34-0), densipolic alcohol, lesquerolic alcohol, auricolic alcohol, 9-hydroxymethylstearic alcohol, 10-hydroxymethylstearic alcohol, 12-hydroxystearic alcohol (CAS: 2726-73-0), and mixtures thereof. The dicarboxylic acid of formula (XVI) is preferably chosen from the group consisting of malonic acid (C3), succinic acid (C4), glutaric acid (C5), adipic acid (C6), heptanedioic acid (C7), octanedioic acid (C8), nonanedioic acid (C9), decanedioic acid (C10), undecanedioic acid (C11), dodecanedioic acid (C12), tridecanedioic acid (C13), tetradecanedioic acid (C14), pentadecanedioic acid (C15), hexadecanedioic acid (C16), heptadecanedioic acid (C17), octadecanedioic acid (C18), nonadecanedioic acid (C19), eico-sanedioic acid (C20), heneicosanedioic acid (C21), docosanedioic acid (C22), trocosanedioic acid (C23), tetracosanedioic acid (C24), pentacosanedioic acid (C25), hexacosanedioic acid (C26), hep-tacosanedioic acid (C27), octacosanedioic acid (C28),of nonacosa-nedioic acid (C29), triacontanedioic acid (C30), and their unsaturated and branched analogues, and mixtures thereof. The diols of formula (XV) are preferably chosen from the following compounds and their mixtures: [Chem.31] OH ...-- X - HO" ' ' 'OH

[0240]

[0241]

[0242]

[0243] HO CH HO OH The diols of formula (XV) can be obtained by hydrogenation of the corresponding hydroxyalkanoic compounds according to the process described in WO 2013 / 156341. Preferably, in the above-mentioned formulas (V) and (XV), Rb represents a linear alkyl radical, saturated or unsaturated, comprising from 5 to 14 carbon atoms, even more preferably from 6 to 9 carbon atoms. Polyols of formula (V) are preferably those of formula (VA) or (VB): [Chem. 32]

[0244]

[0245]

[0246]

[0247]

[0248] (VB) in which R5, x, y, z, p, v, w, and are such as defined previously. Preferably, in formulas (V), (VA), and (VB): p is an integer such that the number molecular mass (Mn) of the compound of formula (V) varies from 1,000 to 20,000 g / mol; R5 is an alkylene radical, saturated or unsaturated, comprising from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms and even more preferably from 2 to 6 carbon atoms. The polyol of formula (V) is preferably chosen from the following polyols:

[0249] [Chem.33]

[0250] in which R5 and p are as defined previously. Polyols of formula (VI)

[0251] The polyols of formula (VI) above can be obtained by polycondensation reaction of at least one dicarboxylic acid of formula (XVII), or one of its ester derivatives, with a diol of formula (XVIII):

[0252] [Chem.34]

[0253] (XVII)

[0254] [Chem.35] OH-R6-OH (XVII!)

[0255] in which R6, Rk and s are as defined previously.

[0256] The polycondensation reaction can be carried out by any means known to those skilled in the art, for example in the presence of enzymes or transesterification catalysts known in the field. Preferably, the catalyst is chosen from the group consisting of sodium methoxide, magnesium oxide, zinc acetate, germanium dioxide, titanium tetraalkoxide (such as, for example, titanium tetrabutoxide), and mixtures thereof.

[0257] The polycondensation reaction can be carried out at a temperature ranging from 150°C to 260°C, preferably from 150°C to 240°C, possibly under reduced pressure, for example at about 10 mbar.

[0258] The diol of formula (XVIII) is preferably selected from the group consisting of ethylene glycol (CAS: 107-21-1), diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, 1,6-hexanediol, 1,5-heptanediol, 1,7-heptanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,12-octadecanediol, 3-ethyl-2-methyl-1,5-pentanediol, 2-ethyl-3-propyl-1,5-pentanediol, 2,4-dimethyl-3-ethyl-1,5-pentanediol, 2-ethyl-4-methyl-3-propyl-1,5-pentadiol, 2,3-diethyl-4-methyl-1,5-pentanediol, 3-ethyl-2,2,4-trimethyl-1,5-pentadiol, 2,2-dimethyl-4-ethyl-3-propyl-1,5-pentanediol, 2-methyl-2-propyl-1,5-pentanediol, 2,4-dimethyl-3-ethyl-2-propyl-1,5-pentanediol, 2,3-Dipropyl-4-ethyl-2-methyl-1,5-pentanediol, 2-butyl-2-ethyl-1,5-pentanediol, 2-butyl-2,3-diethyl-4-methyl-1,5-pentanediol, 2-Butyl-2,4-Diethyl-3-propyl-1,5-pentanediol, 3-Butyl-2-propyl-1,5-pentanediol, 2-Methyl-1,5-pentanediol (CAS: 42856-62-2), 3-Methyl-1,5-pentanediol (MPD, CAS: 4457-71-0), 2,2-Dimethyl-1,3-pentanediol (CAS: 2157-31-5), 2,2-Dimethyl-1,5-pentanediol (CAS: 3121-82-2), 3,3-Dimethyl-1,5-pentanediol (CAS: 53120-74-4), 2,3-Dimethyl-1,5-pentanediol (CAS: 81554-20-3), 2,2-Dimethyl-1,3-propanediol (Neopentyl glycol - NPG, CAS: 126-30-7), 2,2-Diethyl-1,3-propanediol (CAS: 115-76-4), 2-Methyl-2-propyl-1,3-propanediol (CAS: 78-26-2), 2-Butyl-2-ethyl-1,3-propanediol (CAS: 115-84-4), 2-Methyl-1,3-propanediol (CAS: 2163-42-0), 2-Benzyloxy-1,3-propanediol (CAS: 14690-00-7), 2,2-Dibutyl-1,3-propanediol (CAS: 24765-57-9), 2,2-Diisobutyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 2-Ethyl-1,6-Hexanediol (CAS: 15208-19-2), 2,5-Dimethyl-1,6-Hexanediol (CAS: 49623-11-2), 5-Methyl-2-(l-Methylethyl)-l,3-Hexanediol (CAS: 80220-07-1), 1,4-Dimethyl-1,4-Butanediol, 1,5-Hexanediol (CAS: 928-40-5), 3-Methyl-1,6-hexanediol (CAS: 4089-71-8), 3-tert-butyl-1,6-hexanediol (CAS: 82111-97-5), 1,3-heptanediol (CAS: 23433-04-7), 1,2-octanediol (CAS: 1117-86-8), 1,3-octanediol (CAS: 23433-05-8), 2,2,7,7-tetramethyl-1,8-octanediol (CAS: 27143-31-3), 2-methyl-1,8-octanediol (CAS: 109359-36-6), 2,6-dimethyl-1,8-octanediol (CAS: 75656-41-6), 1,7-octanediol (CAS: 3207-95-2), 4,4,5,5-tetramethyl-3,6-dioxa-1,8-octanediol (CAS: 76779-60-7), 2,2,8,8-tetramethyl-1,9-nonanediol (CAS: 85018-58-2), 1,2-nonanediol (CAS: 42789-13-9), 2,8-Dimethyl-1,9-nonanediol (CAS: 40326-00-9), 1,5-nonanediol (CAS: 13686-96-9), 2,9-dimethyl-2,9-dipropyl-1,10-decanediol (CAS: 85018-64-0), 2,9-Dibutyl-2,9-Dimethyl-1,10-decanediol (CAS: 85018-65-1), 2,9-Dimethyl-2,9-Dipropyl-1,10-decanediol (CAS: 85018-64-0), 2,9-Diethyl-2,9-Dimethyl-1,10-decanediol (CAS: 85018-63-9), 2,2,9,9-tetramethyl-1,10-decanediol (CAS: 35449-36-6), 2-nonyl-1,10-decanediol (CAS: 48074-20-0), 1,9-decanediol (CAS: 128705-94-2), 2,2,6,6,10,10-hexamethyl-4,8-dioxal-1,11-undecanediol (CAS: 112548-49-9), 1-phenyl-1,11-undecanediol (CAS: 109217-58-5), 2-octyl-1,11-undecanediol (CAS: 48074-21-1), 2,10-diethyl-2,10-dimethyl-1,11-undecanediol (CAS: 85018-66-2), 2,2,10,10-tetramethyl-1,11-undecanediol (CAS: 35449-37-7), 1-phenyl-1,11-undecanediol (CAS: 109217-58-5), 1,2-undecanediol (CAS: 13006-29-6), 1,2-dodecanediol (CAS: 1119-87-5), 2,11-dodecanediol (CAS: 33666-71-6), 2,11-diethyl-2,11-dimethyl-1,12-dodecanediol (CAS: 85018-68-4), 2,11-dimethyl-2,11-dipropyl-1,12-dodecanediol (CAS: 85018-69-5), of 2,ll-dibutyl-2,ll-dimethyl-1,12-dodecanediol (CAS: 85018-70-8), of 2,2,11,1-tetramethyl-1,12-dodecanediol (CAS: 5658-47-9), 1,11-dodecanediol (CAS: 80158-99-2), 11-methyl-1,7-dodecanediol (CAS: 62870-49-9), 1,4-dodecanediol (CAS: 38146-95-1), 1,3-dodecanediol (CAS: 39516-24-0), 1,10-dodecanediol (CAS: 39516-27-3), 2,11-dimethyl-2,11-dodecanediol (CAS: 22092-59-7), 1,5-dodecanediol (CAS: 20999-41-1), 6,7-dodecanediol (CAS: 91635-53-9), cyclohexanedimethanol, hydrogenated bisphenol A, cyclo-hexanediol, ricinoleic alcohol, and mixtures thereof.

[0259] Preferably, in formulas (VI) and (XVIII), R6 is an alkylene radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms, even more advantageously from 2 to 20 carbon atoms.

[0260] The dicarboxylic acids of formula (XVII) are preferably selected from the following compounds and mixtures thereof:

[0261] [Chem.36] O o HQ " 'OH

[0262] The dicarboxylic acids of formula (XVII) can be obtained by catalytic conversion of the corresponding formylalkanoic acids according to the process described in US 3,804,895.

[0263] Polyols of formula (VI) are preferably those of formula (VLA) and (VLB):

[0264] [Chem.37] (VIA)

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275] (VI-B) in which R6 and u are as defined previously. Composition G1 The hydroxyl number (IOH) of polyol A2, and more generally of a polyol, represents the number of hydroxyl groups per gram of polyol and is expressed as the equivalent number of milligrams of potassium hydroxide (KOH) used in the determination of hydroxyl groups, as determined by titration according to ISO 14900:2017. The IOH is related to the number-average molecular weight (Mn) by the following equation: [math 1] IOH = (fn x 1000 x 56.11) / Mn where fn is the average functionality of the chains, and Mn is the average molecular mass. Polyol A2 can have an IOH ranging from 6 to 187 mg KOH / g, preferably from 11 to 112 mg KOH / g, preferably from 19 to 112 mg KOH / g and even more preferably from 28 to 95 mg KOH / g. Preferably, composition G1 comprises at least one A2 polyol selected from polyols of formula (I) and their mixtures. The hydroxyl index IOH of composition G1 can range from 5 to 187 mg KOH / g, preferably from 11 to 112 mg KOH / g and even more preferably from 30 to 95 mg KOH / g. Preferably, composition G1 comprises more than 80% by weight of A2 polyol(s), more preferably more than 90% by weight, and even more preferably more than 95% by weight of A2 polyol(s).

[0276] Preferably, composition G1 does not include polypropylene glycol, and even more preferably does not include polyether polyol.

[0277] Preferably, composition G1 does not comprise polyolefin polyol. Component - NCO

[0278] The -NCO component is a composition comprising at least one polyurethane obtained by polyaddition reaction from a G1 composition comprising at least one A2 polyol and a G2 composition comprising at least one polyisocyanate, Composition G2

[0279] Composition G2 may comprise a polyisocyanate or a mixture of different polyisocyanates.

[0280] The polyisocyanate may be selected from diisocyanates, triisocyanates and mixtures thereof.

[0281] Examples of diisocyanates include the group consisting of isophorone diisocyanate (IPDI), pentamethylene diisocyanate (PDI), hexamethylene diisocyanate (HDI), heptane diisocyanate, octane diisocyanate, nonane diisocyanate, decane diisocyanate, undecane diisocyanate, dodecane diisocyanate, 4,4'-methylenebis(cyclohexylisocyanate) (4,4'-HMDI), norbomene diisocyanate, norbomene diisocyanate, 1,4-cyclohexane diisocyanate (CHDI), methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate, and cyclohexane dimethylene. diisocyanate, 1,5-diisocyanato-2-methylpentane (MPDI), 1,6-diisocyanato-2,4,4-trimethylhexane, 1,6-diisocyanato-2,2,4-trimethylhexane (TMDI), 4-isocyanatomethyl-1,8-octane diisocyanate (TIN), (2,5)-bis(isocyanatomethyl)bicyclo[2.2.1]heptane (2,5-NBDI), (2,6)-bis(isocyanatomethyl)bicyclo[2.2.1]heptane (2,6-NBDI), 1,3-bis(isocyanatomethyl)cyclohexane (1,3-H6-XDI), 1,4-bis(isocyanatomethyl)cyclohexane (1,4-H6-XDI), xylylene diisocyanate (XDI) (in particular m-xylylene diisocyanate (m-XDI)), toluene diisocyanate (in particular 2,4-toluene diisocyanate (2,4-TDI) and / or 2,6-toluene diisocyanate (2,6-TDI)), diphenylmethane diisocyanate (in particular 4,4'-diphenylmethane diisocyanate (4,4'-MDI) and / or 2,4'-diphenylmethane diisocyanate (2,4'-MDI)), tetramethylxylylene diisocyanate (TMXDI) (in particular the tetramethyl (meta)xylylene diisocyanate), of an allophanate of PDI (n = 5) or of HDI (n = 6) having for example the following formula (Y): .

[0282] [Chem.38]

[0283] (Y)

[0284] in which p is an integer from 1 to 2, q is an integer from 0 to 9, and preferably from 2 to 5, Rc represents a hydrocarbon chain, saturated or unsaturated, cyclic or acyclic, linear or branched, comprising from 1 to 20 carbon atoms, preferably from 6 to 14 carbon atoms, Rd represents a divalent alkylene group, linear or branched, having from 2 to 4 carbon atoms, and preferably a divalent propylene group;

[0285] and mixtures thereof.

[0286] The diisocyanates are preferably aromatic diisocyanates, arylaliphatic or cycloaliphatic diisocyanates.

[0287] Preferably, the diisocyanates are selected from toluene diisocyanate (in particular 2,4-toluene diisocyanate (2,4-TDI) and / or 2,6-toluene diisocyanate (2,6-TDI)), diphenylmethane diisocyanate (in particular 4,4'-diphenylmethane diisocyanate (4,4'-MDI) and / or 2,4'-diphenylmethane diisocyanate (2,4'-MDI)), isophorone diisocyanate (IPDI), xylylene diisocyanate (XDI) (in particular m-xylylene diisocyanate (m-XDI)), allophanes of HDI or PDI, and mixtures thereof.

[0288] Among the triisocyanates, examples include isocyanurates, biurets, and diisocyanate and triol adducts.

[0289] Isocyanurates may be used in the form of a technical mixture of (poly)isocyanurate(s) of purity greater than or equal to 70% by weight isocyanurate(s).

[0290] Examples of diisocyanate trimers include: - the hexamethylene diisocyanurate (HDI) isocyanurate trimer:

[0291] [Chem.39] NCO OCN ^CH^-NCO O isocyanurate trimer of isophorone diisocyanate (IPDI):

[0292] [Chem.40]

[0293] By way of example of diisocyanate and triol adducts usable according to the invention, mention may be made of the meta-xylylene diisocyanate and trimethylolpropane adduct, as shown below. This adduct is marketed, for example, by MITSUI CHEMICALS, Inc. under the name "TAKENATE® D-110N":

[0294] [Chem.41] CHS-CH2-C-[CH2-O-Ç(=O)-W-CH2.J^

[0295] Polyisocyanates are widely available commercially. For example, there is "SCURANATE® TX" marketed by VENCOREX, corresponding to a 2,4-TDI with a purity of around 95%, "SCURANATE® T100" marketed by VENCOREX, corresponding to a 2,4-TDI with a purity greater than 99% by weight, and "DESMODUR® I" marketed by COVESTRO, corresponding to an IPDI.

[0296] According to a preferred embodiment, the polyisocyanate is an aromatic diisocyanate, and even more preferably it is diphenylmethane diisocyanate.

[0297] Diphenylmethane diisocyanate may comprise at least 4% by weight of the 4,4' isomer on the basis of its total weight.

[0298] Examples include Isonate® M125 from DOW, which has a 4,4' isomer content of at least 97% by weight and a 2,2' isomer content of less than 0.1%. The -NCO group percentage of this product (expressed by weight) is 33.6%; LUPRANAT MIPS, available from BASF, which is a mixture of 4,4'-MDI and 2,4'-MDI containing between 46.6% and 52.5% by weight of 4,4'-MDI isomer and less than 0.2% by weight of 2,2'-MDI isomer, with a mass content of 33.5% of the NCO isocyanate group; and WANNATE MDL10, marketed by WANHUA, which has a 4,4' isomer content of 4 to 12%.

[0299] Composition G2 may comprise more than 90% by weight of polyisocyanate(s), of preferably more than 95% by weight, preferably more than 99% by weight, and even more preferably it is made up of polyisocyanate(s). Polyaddition step

[0300] The polyaddition reaction can be carried out at a temperature below 95°C, for example between 50°C and 80°C.

[0301] The polyaddition reaction can be carried out in quantities such that the NCO / OH molar ratio (rl) ranges from 1.3 to 8, preferably from 1.5 to 5.5.

[0302] In the context of the invention, and unless otherwise stated, (rl) is the NCO / OH molar ratio corresponding to the molar ratio of the number of isocyanate groups (NCO) to the number of hydroxyl groups (OH) carried by all the polyisocyanate(s) and polyol(s) present in the reaction medium.

[0303] The polyaddition reaction can be carried out in the presence or absence of at least one reaction catalyst.

[0304] The catalyst can be any catalyst known to a person skilled in the art to catalyze the formation of polyurethane by reaction of at least one polyisocyanate with at least one polyol.

[0305] Up to 0.3% by weight of catalyst(s) relative to the weight of the reaction medium may be used.

[0306] The reaction can also be carried out in the presence of a solvent. The solvent can be chosen from the group consisting of esters, ketones, aromatic compounds, and mixtures thereof. The solvent can be added to, or can be derived from, the starting reagents in solution in said solvent. The solvent can, for example, be chosen from the group consisting of esters, ketones, aromatic compounds, and mixtures thereof. The solvent can, for example, be chosen from ethyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, acetone, toluene, xylene, and mixtures thereof.

[0307] Polyurethane (dry extract) may have a mass percentage of NCO groups ranging from 1% to 20% by weight, preferably from 2% to 15% by weight relative to the total weight of polyurethane. Component -NCO

[0308] The -NCO component may comprise from 20% to 100% by weight, preferably from 30% to 100% by weight, more preferably from 40% to 100% by weight of polyurethane(s) (dry extract) relative to the total weight of said -NCO component.

[0309] Polyurethane can be a single polymer or a mixture of polymers.

[0310] Viscosity measurement at 23°C or 40°C can be carried out using a viscometer Brookfield according to ISO 2555 published in 2018. Typically, the measurement at 23°C or 40°C can be taken using a Brookfield RVT viscometer and a needle. adapted to the viscosity range and to a rotation speed also adapted to the viscosity range.

[0311] The -NCO component may include at least one additive selected from the group consisting of plasticizers, catalysts, rheological agents, solvents, pigments, adhesion promoters, moisture absorbers, UV stabilizers (or antioxidants), colorants, fillers, and mixtures thereof.

[0312] By way of example of a usable plasticizing agent, any plasticizing agent commonly used in the field of adhesives may be cited, such as, for example, epoxy resins, phthalates, benzoates, trimethylolpropane esters, trimethylolethane esters, trimethylolmethane esters, glycerol esters, pentaerythritol esters, naphthenic mineral oils, adipates, cyclohexyldicar-boxylates, paraffinic oils, natural oils (possibly epoxidized), polypropylenes, polybutylenes, hydrogenated polyisoprenes, and mixtures thereof.

[0313] The -NCO component may comprise at least one solvent, for example in an amount from 0% to 60% by weight, preferably from 0% to 50% by weight, and even more preferably from 0 to 45% by weight, relative to the total weight of the -NCO component.

[0314] The solvent can be chosen from organic and alcoholic solvents such as ethyl acetate, acetone, methyl ethyl ketone, xylene, ethanol, isopropanol, tetrahydrofuran, methyl tetrahydrofuran, or from "ISANE®" (based on isoparaffins, available from TOTAL) or "EXXOL® D80" (based on aliphatic hydrocarbons, available from EXXON MOBIL CHEMICAL).

[0315] The solvent-free -NCO component (dry extract) may have a viscosity at 40°C ranging from 400 mPa.s to 6000 mPa.s, preferably 500 mPa.s to 5000 mPa.s.

[0316] The solvent-based -NCO component (60% dry extract) may have a viscosity at 23°C ranging from 20 to 6000 mPa.s, preferably 50 to 5000 mPa.s.

[0317] The solvent-based -NCO component (70% dry extract) may have a viscosity at 23°C of less than 8000 mPa.s, preferably less than 6000 mPa.s.

[0318] The solvent-based -NCO component (75% dry extract) may have a viscosity at 23°C of less than 12000 mPa.s, preferably less than 9000 mPa.s.

[0319] In the context of the invention, "solventized -NCO component" means an -NCO component comprising at least one solvent. COMPONENT -OH

[0320] The -OH component may comprise at least 80% by weight of Al polyol or a mixture of different Al polyols (dry extract).

[0321] The Al polyol can be selected from:

[0322] - a polyol of formula (I), (II), (BI-1), (III-2), (BI-3), (IV-1), (IV-2), (IV-3), (V) or (VI) as defined above,

[0323] - a hydroxylated triglyceride polyol extracted from natural plant materials or genetically modified (e.g. castor bean, camelina, palm tree, legume, Les-querella, brassica or brassicaceae),

[0324] - a polyol derived from the hydroxylation of unsaturated vegetable oils,

[0325] - a polyol derived from the hydroxymethylation of unsaturated vegetable oils, or

[0326] - their mixtures.

[0327] Preferably, the Al polyol is a hydroxylated triglyceride type polyol derived from naturally hydroxylated vegetable oil.

[0328] Castor oil is a vegetable oil obtained from castor seeds, and consists of triglycerides (tristers of fatty acids), said fatty acids comprising approximately 90% by weight of a monounsaturated and hydroxylated Cl8 fatty acid: ricinoleic acid.

[0329] The triglyceride of ricinoleic acid has the following formula:

[0330] [Chem.42] OH

[0331] Preferably, the -OH component does not comprise a polyol having a number molecular mass Mn less than or equal to 500 g / mol.

[0332] Preferably, the -OH component comprises only triglyceride-type polyols derived from vegetable oil, and even more preferably from castor oil.

[0333] The -OH component may include at least one additive selected from the group consisting of plasticizers, catalysts, rheological agents, solvents, pigments, adhesion promoters, moisture absorbers, UV stabilizers (or antioxidants), colorants, fillers, and mixtures thereof.

[0334] By way of example of a usable plasticizing agent, any plasticizing agent commonly used in the field of adhesives may be cited, such as, for example, epoxy resins, phthalates, benzoates, trimethylolpropane esters, trimethylolethane esters, trimethylolmethane esters, glycerol esters, pentaerythritol esters, naphthenic mineral oils, adipates, cyclohexyldicar-boxylates, paraffinic oils, natural oils (possibly epoxidized), polypropylenes, polybutylenes, hydrogenated polyisoprenes, and mixtures thereof.

[0335] The non-solventized -OH component (dry extract) may have a viscosity at 35°C ranging from 10 mPa.s to 3000 mPa.s, preferably 100 mPa.s to 2000 mPa.s.

[0336] Viscosity measurement at 35°C can be carried out using a Brookfield viscometer according to ISO 2555 published in 2018. Typically, the measurement carried out at 35°C can be carried out using a Brookfield RVT viscometer, a needle adapted to the viscosity range and a rotation speed also adapted to the viscosity range.

[0337] The -OH component may comprise at least one solvent, for example in an amount from 0% to 60% by weight, preferably from 0% to 50% by weight, and even more preferably from 0 to 45% by weight, relative to the total weight of the -OH component.

[0338] Preferably, the -OH component does not comprise polyolefin polyol. Adhesive composition CA

[0339] The quantities of the components -NCO and -OH in said CA adhesive composition may be such that the equivalent molar ratio -NCO / -OH is in a range from 1.5 to 5.0, preferably from 1.5 to 4.0, and even more preferably from 1.5 to 3.0.

[0340] The molar equivalent ratio -NCO / -OH is understood to mean the ratio of the equivalent number of -NCO groups (present in the -NCO component) to the equivalent number of -OH groups (present in the -OH component).

[0341] The adhesive composition CA may include at least one additive selected from the group consisting of plasticizers, catalysts, rheological agents, solvents, pigments, adhesion promoters, moisture absorbers, UV stabilizers (or antioxidants), colorants, fillers, and mixtures thereof.

[0342] These additives may be found in the -NCO component, in the -OH component or in both.

[0343] When the CA adhesive composition is solvent-based, this means that it includes at least one solvent.

[0344] The implementation of the CA adhesive composition, when solvent-based, in a laminating process necessitates an evaporation step of the organic solvent. This step is typically carried out before the laminating step by passing the first adhesive-coated film, following the coating step, through an oven.

[0345] The CA adhesive composition is typically supplied to the complexer in the form of 2 compositions (or components):

[0346] - one (called component -NCO) comprising chemical entities carrying terminal isocyanate groups -NCO, and

[0347] - the other (called component -OH) comprising chemical entities carrying terminal hydroxyl groups -OH.

[0348] The mixing of these two components can be carried out at 23°C if the composition is solvent-based, otherwise between 35 and 60°C, by the operator of the laminating machine prior to its start-up, thus ensuring its correct operation thanks to an appropriate viscosity. The viscosity of the adhesive composition thus obtained can be adjusted by simply adding solvent by the operator when it is solvent-based, resulting in a final quantity of dry extract of the adhesive composition which can vary in practice from 30 to 70% w / w, preferably from 30 to 55% w / w; otherwise, by adjusting the application temperature.

[0349] Following the step of coating the mixture thus obtained on the 1st thin layer, and the step of counter-bonding the 2nd layer, the isocyanate groups of the -NCO component react with the hydroxyl groups of the -OH component, to form a polyurethane which typically takes the form of a three-dimensional network with methane groups (cross-linked) or a branched polyurethane, ensuring the cohesion of the adhesive joint between the 2 laminated thin layers.

[0350] The adhesive layer of the Fl multilayer system can be obtained by reacting all the NCO functions of the aforementioned CA adhesive composition in an amount ranging from 0.5 to 5 g / m². Preferably, the amount ranges from 1.3 to 5 g / m², and even more preferably from 1.5 to 5 g / m². Fl multilayer system

[0351] The multilayer system Fl may further comprise one or more additional layers (in addition to the aforementioned Cl, A and C2 layers).

[0352] These may be barrier layers (for example, protein-based layers, aluminum oxide (AIOx)-based layers, silicon oxide (SiOx)-based layers, aluminum, PVOH (PolyVinyl Alcohol), ethylene-vinyl alcohol (EVOH) copolymers, ethylene-alkyl acrylate copolymers, ethylene-vinyl acetate (EVA) copolymers...), bonding layers (called intermediate layers or "tie layers" in English), printable layers, etc.

[0353] The total thickness of the Fl multilayer system may be likely to vary in a wide range, for example from 20 to 400 pm.

[0354] Preferably, the multilayer system Fl comprises at least 92%, preferably at least 95% by weight, and even more preferably at least 97% by weight of polyolefin or a mixture of polyolefins relative to the total weight of said system.

[0355] The multilayer system Fl can be obtained by any process known in the field. When it is a laminate, it can be obtained by a lamination (bonding) process. Bonding processes typically include the following steps: - the application of an adhesive composition to a first layer (by (example on the aforementioned Cl layer) in the form of a substantially continuous layer, - the lamination of a second layer (for example, layer C2) onto the first coated layer, - the reaction of the adhesive composition.

[0356] Such a process is described for example in WO2020 / 217023.

[0357] The Fl multilayer system is preferably a food packaging or cosmetic packaging. Recycled item

[0358] The recycled article is preferably a single-layer film or a laminate or a complex (multilayer), more preferably a single-layer film.

[0359] In the context of the invention, "single-layer film" means a film comprising a single layer, and is thus distinguished from multi-layer films.

[0360] The recycled article is preferably obtained by mechanical recycling of the multilayer system Fl according to the invention.

[0361] The recycled article preferably comprises a reaction product between an -NCO component and an -OH component, in a content less than or equal to 5% by weight, preferably less than or equal to 3%, and even more preferably less than or equal to 2.5% by weight relative to the total weight of said recycled article. The recycled article comprises a reaction product between an -NCO component and an -OH component, therefore its content is non-zero in this preferred case.

[0362] The recycled article preferably comprises from 0.45% to 5% by weight of a reaction product between an -NCO component and an -OH component, preferably from 0.50% to 3% by weight, and even more preferably from 0.50% to 2.50% by weight relative to the total weight of said recycled article.

[0363] Various methods known to those skilled in the art can be used to determine the presence of a reaction product between an -NCO component and an -OH component. For example, mass spectrometry can be used, which allows for structural and quantitative analysis.

[0364] Various methods known to those skilled in the art allow for the determination of the content of the reaction product between an -NCO component and an -OH component. For example, this can be done by elemental microanalysis, more particularly to quantify the contents of nitrogen (N) and oxygen (O) atoms.

[0365] The recycled article preferably comprises at least 95%, more preferably at least 97%, even more preferably at least 97.5% by weight of polyolefin or a mixture of polyolefins relative to the total weight of said recycled article.

[0366] The definition, embodiments and preferred modes of polyolefins described above apply to the recycled article without the need to describe them further. new.

[0367] From 0% to 99.55% of the total polyolefin(s) present in the recycled article may be virgin polyolefins, for example from 0% to 95%, from 0% to 90%, from 0% to 85%, from 0% to 75%, from 0% to 70%, from 0% to 65%, from 0% to 60%, from 0% to 55%, from 0% to 50%, from 0% to 45%, from 0% to 40%, from 0% to 35%, from 0% to 30%, from 0% to 30%, from 0% to 25%, from 0% to 20%, from 0% to 15%, from 0% to 10%.

[0368] In the context of the invention, and unless otherwise stated, "virgin polyolefin" means a newly produced polyolefin that has not been recycled.

[0369] The recycled article advantageously has a Haze value of less than or equal to 20%, preferably from 5 to 15%, more preferably from 5 to 12%.

[0370] The Haze value is measured according to ASTM D1003 in white with an observation degree of 10°C and a D65 light source from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0371] The recycled article advantageously has a gloss of less than or equal to 20%, preferably from 5 to 15%, more preferably from 5 to 12%.

[0372] Brightness / whitening can be measured according to ISO 2470 in the dark with an observation angle of 10° and a D65 light source from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0373] The recycled article advantageously has a luminance L* less than or equal to 50, preferably from 20 to 45, more preferably from 20 to 40.

[0374] Luminance (L*) can be measured in the dark, in CieLab space (opposite color coordinate system, with an observation degree of 10° and a D65 light source, from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0375] The recycled article advantageously has a transparency Y of less than or equal to 25%, preferably from 5 to 20%, more preferably from 5 to 15%.

[0376] Transparency (Y) can be measured according to ASTM D1003 in the dark with a degree of observation of 10° and a light source D65 from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0377] The recycled article advantageously has a yellow coloration b* less than or equal to 0.27, preferably from 0.10 to 0.25, more preferably from 0.15 to 0.25.

[0378] The yellow b* colouring can be measured in white, in CieLab space (opposite colour coordinate system, with an observation degree of 10° and a D65 light source, from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0379] The recycled article advantageously has a saturation C* less than or equal to 0.30, preferably from 0.10 to 0.30, more preferably from 0.15 to 0.25.

[0380] The saturation C* can be measured in white with an observation angle of 10° and a D65 light source, from a KONICA MINOLTA CM5 type spectrocolorimeter.

[0381] The recycled article advantageously presents a limited or even zero content of gels / unmelted material.

[0382] The recycled article advantageously has an elongation at break of 100 to 900%, preferably of 200 to 850%, more preferably of 300 to 850%, measured according to ISO 527-3, for a thickness of 35-45 microns (specimen dimensions 33x6 mm2, tensile speed 50 mm / min).

[0383] The recycled article advantageously has a tensile strength of 8 to 60 MPa, preferably of 10 to 55 MPa, more preferably of 15 to 50 MPa, measured according to ISO 527-3, for a thickness of 35-45 microns (specimen dimensions 33x6 mm2, tensile speed 50 mm / min).

[0384] The recycled article preferably comprises a recycled content of 10% or more, more preferably 25% or more, and more advantageously 50% or more. Recycling process for a Fl system

[0385] The present invention also relates to a mechanical recycling method for a multilayer system Fl comprising: - a Cl layer comprising at least one polyolefin, - an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, - a C2 layer comprising at least one polyolefin,

[0386] said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system,

[0387] said process comprising: - i) a step of supplying the Fl multilayer system, and - ii) a grinding step of said FL multilayer system

[0388] The description, embodiments, and preferred modes described above for the Fl multilayer system apply to the recycling process without needing to be repeated. For example, the nature of the polyolefins, as well as the nature of the -NCO and -OH components, apply to the present recycling process and are not repeated.

[0389] Step ii) of grinding advantageously leads to chips (also called "flakes" in English, or "sparkles") of a size preferably between 5 and 25 mm, even more preferably between 8 and 20 mm.

[0390] Step ii) of grinding can be carried out at 23°C.

[0391] The process may include an optional washing step iii-1) of the chips obtained in step ii), and a drying step iii-3).

[0392] The washing step iii-1) can be carried out with water, possibly in the presence of additives, possibly under agitation.

[0393] The washing step iii-1) advantageously allows the removal of residues present in packaging such as, for example, food waste or cosmetic residues from cosmetic packaging, or the removal of any inks that may be present or other.

[0394] The washing step iii-1) can be carried out at a temperature ranging from 20°C to 25°C.

[0395] Typically, the washing step iii-1) can be carried out by adding water, possibly in the presence of additives, in a chip:water ratio ranging from 1:10 to 1:100.

[0396] The process may include a flotation step iii-2) between step ii-1) and step ii-3). This step may be carried out by any means known to a person skilled in the art.

[0397] The chips from the washing step iii-1) can be placed in a stirred tank during or after the washing step. After stirring is stopped, the flotation / separation step advantageously separates the floating products from those (preferably impurities) that settle to the bottom of the stirring tank. The flotation step is typically a density separation step. Polyolefins typically have a density of less than 1 g / cm³, which generally allows them to be recovered from the surface.

[0398] The drying step iii-3) can be carried out by any known method. It can be carried out at a temperature ranging from 50°C to 100°C, preferably from 60°C to 80°C, for a duration ranging from 30 minutes to 24 hours.

[0399] Preferably, the process includes a washing step iii-1), an optional flotation step iii-2), and a drying step iii-3).

[0400] The process may further include an optional densification step iv) of the chips obtained at the end of step ii), or at the end of the drying step iii-3).

[0401] Densification (iv) can be carried out by any method known to those skilled in the art. Densification advantageously makes the chips more homogeneous.

[0402] The process may include an optional step a-1) of mixing the chips obtained at the end of step ii), iii-3) or iv) with chips, powders or granules of virgin PO polyolefin, preferably with chips of virgin PO polyolefin.

[0403] In the context of the invention, and unless otherwise stated, "virgin polyolefin" means a newly produced polyolefin that has not been recycled.

[0404] The term “polyolefin” covers homopolymers and copolymers prepared from olefin monomers.

[0405] Copolymers include, in particular:

[0406] - copolymers obtained from at least two different olefins (for example ethylene-propylene or ethylene-butene copolymers), and

[0407] - copolymers obtained from at least one olefin monomer with at least one co-monomer said copolymers comprising more than 50 mol % of units derived from olefin monomer(s).

[0408] Polyethylene can be selected from linear polyethylene such as HDPE (High Density Polyethylene), linear low-density polyethylene (LLDPE), very low-density polyethylene (VLDPE), ultra-low-density polyethylene (ULDPE), branched polyethylene such as, for example, low-density polyethylene (LDPE), or medium-density polyethylene (MDPE). Such polyethylenes can be prepared by several methods, including polymerization in the presence of a Ziegler-Natta catalyst, metallocene-catalyzed polymerization, or radical polymerization.

[0409] HDPEs may, in particular, have a density ranging from 0.940 to 0.970 g / cm³.

[0410] ULDPEs may, in particular, have a density ranging from 0.890 to 0.905 g / cm³.

[0411] LDPEs may, in particular, have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm³.

[0412] VLDPEs can in particular have a density ranging from 0.905 (exclusive limit) to 0.915 g / cm3.

[0413] LLDPEs can in particular have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm3.

[0414] MDPEs can in particular have a density ranging from 0.926 to 0.940 g / cm3.

[0415] Linear HDPE (High Density Polyethylene) polyethylenes can be oriented polyethylenes such as, for example, MDOPE (Machine Direction Oriented Polyethylene) or BOPE (biaxially oriented Polyethylene).

[0416] There are also commercial polyethylenes, such as for example: LDPE FT5230 available from BOREALIS; LLDPE Dowlex 2045G available from DOW; HDPE 35060E available from DOW.

[0417] Polypropylene can be selected from oriented polypropylene (OPP: “Oriented PolyPropylene”), bi-oriented polypropylene (BOPP: “Bi-axially Oriented Poly-Propylene”), cast polypropylene (cPP: “Cast PolyPropylene”).

[0418] There are also commercial polypropylenes, such as for example RC2472 available from HMC Polymers; RD226CF available from BOREALIS; ELTEX P available from INEOS.

[0419] The PO polyolefin may be chemically identical or different from the polyolefin of layer Cl or C2 of the FL multilayer system. For example, the PO polyolefin is MDPE polyethylene, the Cl layer polyolefin is LLDDPE polyethylene, and the C2 layer polyolefin is HDPE polyethylene. it is of the same chemical nature (polyethylene).

[0420] The physico-chemical characteristics of the PO polyolefin may be identical or different from those of the Cl and / or C2 layer polyolefin.

[0421] Preferably, the PO polyolefin has a chemical nature identical to that of the Cl and C2 layers.

[0422] Even more preferably, the PO polyolefin is an LDPE polyethylene.

[0423] The mixing step a-1) can be carried out according to a ratio of chips obtained in step ii), iii-3) or iv): chips (powder or granules) of virgin PO polyolefin ranging from 99:1 to 1:99, preferably from 80:20 to 20:80, and even more preferably from 75:25 to 25:75.

[0424] Preferably, the process further includes an extrusion / granulation step v) to obtain granules.

[0425] This step can be done: - on the shavings from step ii); - on the chips from step iii-3); - on the densified chips from step iv); - on the chips from step a-1).

[0426] Typically, the extrusion / granulation step v) comprises: - mixing the chips at a temperature greater than or equal to their melting temperature (this step advantageously allows the chips to melt); - possible filtration, - extrusion in the form of granules.

[0427] The mixing can be carried out at a temperature ranging from 100°C to 250°C, preferably from 120°C to 230°C.

[0428] Filtration can be carried out with a 100-150 micron filter, preferably at a temperature ranging from 100°C to 250°C.

[0429] Extrusion / granulation v) is typically carried out in an extruder, which may include a filter enabling filtration within the extruder itself.

[0430] The recycling process may further include a step of mixing a-2) the granules obtained in step v) with virgin PO polyolefin granules.

[0431] In the context of the invention, and unless otherwise stated, "virgin polyolefin" means a newly produced polyolefin that has not been recycled.

[0432] The term “polyolefin” covers homopolymers and copolymers prepared from olefin monomers.

[0433] Copolymers include, in particular:

[0434] - copolymers obtained from at least two different olefins (for example ethylene-propylene or ethylene-butene copolymers), and

[0435] - copolymers obtained from at least one olefin monomer with at least one co-monomer said copolymers comprising more than 50 mol % of units derived from olefin monomer(s).

[0436] Polyethylene can be selected from linear polyethylene such as HDPE (High Density Polyethylene), linear low-density polyethylene (LLDPE), very low-density polyethylene (VLDPE), ultra-low-density polyethylene (ULDPE), branched polyethylene such as, for example, low-density polyethylene (LDPE), or medium-density polyethylene (MDPE). Such polyethylenes can be prepared by several methods, including polymerization in the presence of a Ziegler-Natta catalyst, metallocene-catalyzed polymerization, or radical polymerization.

[0437] HDPEs may, in particular, have a density ranging from 0.940 to 0.970 g / cm³.

[0438] ULDPEs may, in particular, have a density ranging from 0.890 to 0.905 g / cm³.

[0439] LDPEs may, in particular, have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm³.

[0440] VLDPEs can in particular have a density ranging from 0.905 (exclusive limit) to 0.915 g / cm3.

[0441] LLDPEs can in particular have a density ranging from 0.915 (exclusive limit) to 0.935 g / cm3.

[0442] MDPEs can in particular have a density ranging from 0.926 to 0.940 g / cm3.

[0443] Linear HDPE (High Density Polyethylene) may be oriented polyethylenes such as, for example, MDOPE (Machine Direction Oriented Polyethylene) or BOPE (biaxially oriented Polyethylene).

[0444] There are also commercial polyethylenes, such as for example: LDPE FT5230 available from BOREALIS; LLDPE Dowlex 2045G available from DOW; HDPE 35060E available from DOW.

[0445] Polypropylene can be selected from oriented polypropylene (OPP: “Oriented PolyPropylene”), bi-oriented polypropylene (BOPP: “Bi-axially Oriented Poly-Propylene”), cast polypropylene (cPP: “Cast PolyPropylene”).

[0446] There are also commercial polypropylenes, such as for example RC2472 available from HMC Polymers; RD226CF available from BOREALIS; ELTEX P available from INEOS.

[0447] The PO polyolefin may be chemically identical or different from the polyolefin of layer Cl or C2 of the FL multilayer system. For example, the PO polyolefin is MDPE polyethylene, the polyolefin of layer Cl is LLDDPE polyethylene, and the polyolefin of layer C2 is HDPE polyethylene. it is of the same chemical nature (polyethylene).

[0448] The physico-chemical characteristics of the PO polyolefin may be identical or different from those of the Cl and / or C2 layer polyolefin.

[0449] Preferably, the PO polyolefin has a chemical nature identical to that of the Cl and C2 layers.

[0450] Even more preferably, the PO polyolefin is an LDPE polyethylene.

[0451] According to a preferred mode, either the process includes step a-1), or it includes step a-2). Preferably, it includes the aforementioned step a-2).

[0452] In any event, at the end of step v) or a-2), a granule composition is obtained.

[0453] Preferably, the granule composition obtained at the end of step v) or a-2) comprises a polyolefin and a reaction product between an -NCO component and an -OH component, in a content less than or equal to 5% by weight, preferably less than or equal to 3%, and even more preferably less than or equal to 2.5% by weight relative to the total weight of said composition. Since said granule composition comprises a reaction product between an -NCO component and an -OH component, its content is therefore non-zero in this preferred mode.

[0454] The granule composition obtained at the end of step v) or a-2) preferably comprises from 0.5% to 5% by weight of a reaction product between an -NCO component and an -OH component, preferably from 0.6% to 3% by weight, and even more preferably from 0.6% to 2.5% by weight relative to the total weight of said composition.

[0455] The composition preferably comprises at least 95%, more preferably at least 97%, even more preferably at least 97.5% by weight of polyolefin or a mixture of polyolefins relative to the total weight of said composition.

[0456] The recycling process advantageously includes a step of shaping vi) the pellet composition obtained in the aforementioned step v) or a-2) into a recycled article.

[0457] The shaping step vi) is preferably an extrusion or co-extrusion step vi) of the granule composition obtained in step v) or a-2) to form a single-layer or multi-layer recycled article.

[0458] In the case of a single-layer recycled article, the granule composition is typically fed into an extruder.

[0459] The extrusion is advantageously a bubble blow extrusion (also known as "sheath blow extrusion"). In a manner known to those skilled in the art, this process typically comprises:

[0460] - the melting in an extruder of the granule composition obtained in step v) or a-2),

[0461] - the passage of the corresponding flux through an annular and concentric die, of in order to form a tubular bubble, then

[0462] - radial expansion (relative to the annular channel) and stretching (in the direction axial) of the bubble, then

[0463] - the cooling of the bubble.

[0464] In the case of a multilayer recycled article, the granule composition obtained in step v) or a-2), as well as the compositions and materials constituting the other layers (preferably in granule form), are typically fed into a co-extrusion device.

[0465] Co-extrusion is advantageously bubble-blowing co-extrusion. As is known to those skilled in the art, this process comprises:

[0466] - the melting, in separate extruders, of the constituent compositions and materials of the different layers, then

[0467] - the passage of the corresponding flows through a set of annular channels and concentric, so as to form a multi-layered tubular bubble, in the order corresponding to that desired for the final structure, then

[0468] - radial expansion (relative to the annular channel) and stretching (in the direction axial) of the bubble, then

[0469] - the cooling of the bubble.

[0470] The geometric characteristics of the dies, as well as the process parameters such as the radial expansion rate and the stretching speed, are fixed to obtain the desired thickness for the various constituent layers of the multilayer film. Reference is made, in particular, to US patent application 2013 / 0029553 for a more detailed description of the bubble-blowing co-extrusion process.

[0471] Preferably, the recycling process according to the invention comprises: - i) a step of supplying the Fl multilayer system, - ii) a grinding step of said multilayer system Fl, - iii-1) a step of washing the chips obtained in step ii), an op step flotation function iii-2), and a drying step iii-3), - iv) an optional densification step; - v) an extrusion / granulation step of the chips obtained in the previous step; - a-2) a step of mixing the granules obtained in step v) with granules virgin PO polyolefin; - vi) a step of shaping the granule composition obtained in step a-2) into a recycled article.

[0472] The mechanical recycling process of the Fl multilayer system advantageously leads to a recycled article that can advantageously be reused for further use. The process advantageously allows for a transformation of the system multilayer Fl in chips or granules that can be reused to manufacture a new item. Recycled item

[0473] The description, embodiments, and preferred modes previously disclosed for the recycled article (in the chapter "use of an Fl system") apply in the present process without the need to repeat them. Process for preparing a recycled article / film

[0474] The present invention also relates to a method for preparing a recycled article comprising: - i) a step of supplying a multilayer system Fl comprising: • a Cl layer comprising at least one polyolefin, • an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, • a layer C2 comprising at least one polyolefin,

[0475] said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system, - ii) a grinding step of said multilayer system Fl, - v) an extrusion / granulation step of the chips obtained in the step previous; - vi) a step of shaping the granule composition obtained in the previous step into a recycled article.

[0476] The process may include a washing step iii-1), an optional flotation step iii-2), and a drying step iii-3).

[0477] The process may include an optional densification step iv).

[0478] The process may further include an optional step a-1) of mixing the chips obtained at the end of step ii), iii-3) or iv) with chips, powders or granules of virgin PO polyolefin, preferably virgin PO polyolefin chips.

[0479] The recycling process may further include a step of mixing a-2) the granules obtained in step v) with virgin PO polyolefin granules.

[0480] The definitions, embodiments and preferred modes of steps i), ii), iii-1), iii-2), iii-3), iv), v), vi), a-1) and a-2) of the recycling process defined above for the process of recycling the Fl multilayer system, and the definitions, embodiments and preferred modes of the Fl multilayer system as such, apply to the process of preparing a recycled article without the need to reiterate them.

[0481] Preferably, the process for preparing a recycled article according to the invention comprises: - i) a step of supplying a multilayer Fl system, - ii) a grinding step of said multilayer system Fl, - iii-1) an optional step of washing the chips obtained in step ii), an optional flotation step iii-2), and an optional drying step iii-3), - iv) an optional densification step; - v) an extrusion / granulation step of the chips obtained in the previous step; - a-2) a step of mixing the granules obtained in step v) with granules virgin PO polyolefin; - vi) a step of shaping the granule composition obtained in step a-2) into a recycled article.

[0482] The present invention also relates to the recycled article that can be obtained according to a process comprising: - i) a step of supplying the Fl multilayer system comprising: • a Cl layer comprising at least one polyolefin, • an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, • a layer C2 comprising at least one polyolefin,

[0483] said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system, - ii) a grinding step of said multilayer system Fl, - v) a chip extrusion / granulation step obtained in the step previous; - vi) a step of shaping the granule composition obtained in the previous step into a recycled article.

[0484] The various steps of the process described above apply to the recycled article that can be obtained according to this process. Recycled item

[0485] The description, embodiments, and preferred modes previously disclosed for the recycled article apply in the present process without the need to reiterate them. Uses of an adhesive composition

[0486] The present invention also relates to the use of a CA adhesive composition comprising:

[0487] - an -OH component which is a composition comprising at least one Al polyol;

[0488] - an -NCO component which is a composition comprising at least one polyurethane obtained by polyaddition reaction from a composition G2 comprising at least one polyisocyanate, and a composition G1 comprising at least one polyol A2,

[0489] at least one of the Al or A2 polyols being selected from the following polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), and mixtures thereof:

[0490] [Chem.43]

[0492] (II)

[0494] (III-3) (IV-1)

[0495]

[0496]

[0497] (IV-2) (IV-3) (V)

[0498]

[0499] (VI) in which: R° is a hydrogen, an ethyl or a methyl; R1 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R1 possibly comprising one or more heteroatoms selected from oxygen and sulfur; R2 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R2 possibly comprising one or more heteroatoms selected from oxygen and sulfur; Ra is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; Rb is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; x is an integer representing 0 or 1; y is an integer representing 0 or 1 z is an integer ranging from 1 to 9; s is an integer ranging from 0 to 6; t is an integer ranging from 1 to 4; f is an integer equal to 2 or 3; f is an integer equal to 2 or 3; f and g are integers such that the number molecular mass (Mn) of the compound of formula (I) ranges from 600 to 20,000 g / mol; f' and g' are integers such that the number molecular mass (Mn) of the compound of formula (II) ranges from 600 to 20,000 g / mol; R3 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; R4 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R5 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R6 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; Each carbon-carbon bond, denoted by , represents either a single bond or a double bond. each bond means that the bond is geometrically oriented to one side or the other with respect to the double bond (cis (Z) or trans (E)); n1 is an integer such that the number molecular mass (Mn) of the compound of formula (III-1) ranges from 1000 to 20,000 g / mol; n2 is an integer such that the number molecular mass (Mn) of the compound of formula (III-2) ranges from 1000 to 20,000 g / mol; n3 is an integer such that the number molecular mass (Mn) of the compound of formula (III-3) ranges from 1000 to 20,000 g / mol; m1 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-1) ranges from 1000 to 20,000 g / mol; m2 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-2) ranges from 1000 to 20,000 g / mol; m3 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-3) ranges from 1000 to 20,000 g / mol; p is an integer such that the number molecular mass (Mn) of the compound of formula (V) ranges from 1000 to 20,000 g / mol; u is an integer such that the number molecular mass (Mn) of the compound of formula (VI) ranges from 1,000 to 20,000 g / mol; Rc is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rd is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms;

[0500] or Rc and Rd together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles being optionally substituted by one or more saturated or unsaturated alkyl groups; - Re is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rf is a saturated linear alkyl radical comprising 6 to 8 carbon atoms; - R" is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rh is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms;

[0501] or Rg and Rh together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles being optionally substituted by one or more saturated or unsaturated alkyl groups; - R' is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Ri is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rk is a saturated linear alkyl radical, comprising 6 to 10 carbon atoms;

[0502] to prepare a recycled article.

[0503] The definition, embodiments and preferred embodiments described above for the CA adhesive composition apply in this paragraph without the need to reiterate them.

[0504] Likewise, the definition, embodiments, and preferred modes described above for the recycled article apply in this paragraph without the need to reiterate them.

[0505] Preferably, the recycled article comprises a recycled content of 10% or more, more preferably 25% or more, and more advantageously 50% or more.

[0506] The recycled article can advantageously be reused in various applications such as for example for packaging (e.g. food packaging), plastic bags, bottles / flasks (such as for example for milk, laundry detergent), polyethylene materials.

[0507] The recycled article can be prepared by a mechanical recycling process of a Fl multilayer system as described above.

[0508] The definitions, embodiments and preferred modes of the recycling process defined above for the Fl multilayer system, and of the Fl multilayer system apply to the preparation of the recycled article without the need to reiterate them.

[0509] The present invention also relates to the use of the CA adhesive composition as defined above to recycle at least 25% by weight of a multilayer system, preferably a Fl multilayer system, comprising said CA adhesive composition, to make a recycled article.

[0510] Thus, the present invention relates to the use of the CA adhesive composition as defined above to prepare a recycled article comprising at least 25% by weight of a multilayer system Fl comprising said CA adhesive composition.

[0511] The descriptions, embodiments, and preferred embodiments previously described for the CA adhesive composition, the Fl multilayer system, and the recycled article apply in this paragraph without the need for repetition. Fl multilayer system

[0512] The present invention also relates to a multilayer Fl system comprising: - a Cl layer comprising at least one polyolefin, - an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, said adhesive layer A being obtained from an adhesive composition CA as defined above, - a C2 layer comprising at least one polyolefin,

[0513] said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system.

[0514] The definition, embodiments and preferred modes described above for the CA adhesive composition, the Fl multilayer system apply in this paragraph without the need to reiterate them.

[0515] Within the scope of the present invention, all the embodiments described above can be combined with one another. In particular, the various aforementioned constituents of the CA adhesive composition, and especially the preferred embodiments of the composition, can be combined with one another, as well as with those of the recycling processes, on the FL multilayer system

[0516] In the context of the invention, "between x and y" or "ranging from x to y" means an interval in which the bounds x and y are included. For example, the range "between 0% and 25%" includes, in particular, the values ​​0% and 25%.

[0517] The invention is now described in the following embodiment examples which are given purely for illustrative purposes, and should not be interpreted to limit its scope. Examples:

[0518] The following compounds were used in the examples:

[0519] - Methyl ricinoleate (CAS: 141-24-2) available from ARKEMA

[0520] - Monopropylene glycol or MPG (CAS: 57-55-6) available from BASF (mass molar = 76 g / mol)

[0521] - TIZOR TnBT (CAS: 5593-70-4) available from DORF KETAL, tetra- catalyst n-butyl titanate

[0522] - LUPRANAT MIPS available from BASF, which is a mixture of MDI isomers containing between 46.6% and 52.5% of the 4,4' isomer and less than 0.2% of the 2,2' isomer with a mass content of the isocyanate group NCO of 33.5%

[0523] - POLYCIN™ GR-50 available from Vertellus, polyricinoleate polyol having a Mn equal to 1085 g / mol and an IOH = 52 mg KOH / g and a functionality equal to 2.2

[0524] - POLYCIN™ GR-80 available from Vertellus, polyricinoleate polyol having a Mn equal to 1700 g / mol, an IOH = 75-85 g / mol and a functionality equal to 2.4

[0525] - Castor oil available from VERTELLUS, natural triglyceride having a mass molar mass of 928 g / mol, an IOH of 164 mg KOH / g, and a functionality of 2.7

[0526] Example 1: Preparation of compounds of formula (I) (composition Gl)

[0527] [Chem.44] 995.35 g (3.2 moles) of methyl ricinoleate, 76.09 g (1 mole) of monopropylene glycol, and 0.01 g of Ti(OBu)4 (0.1 wt% of the reactant mixture) are introduced into a 5-liter double-jacketed reactor and heated to 90°C for 30 minutes with light nitrogen bubbling. The reaction mixture is then heated to 200°C under a nitrogen blanket, with mechanical stirring and a partial vacuum of 10 mbar to remove the generated methanol. The condensation reaction is continued for approximately 6 hours until a hydroxyl value of 74 mg KOH / g is obtained.

[0528] Once the reaction is complete, the reaction mixture is cooled to approximately 85°C.

[0529] 872 g of a composition comprising compounds of formula (I) is obtained under the form of a yellow, viscous liquid at room temperature (23°C).

[0530] The quantities are listed in Table 1 below:

[0531] [Tables 1] (in grams) (% by weight) Methyl ricinoleate (312.49 g / mol) 995.35 92.89 Monopropylene glycol (76.09 g / mol) 76.09 7.10 Catalyst Ti(OBu)4 0.1 0.01 100% Experimental IOH of composition (expressed in mg KOH / g) 74 74% Experimental OH* 2.24 2.24

[0532] * OH group content relative to the total weight of the compound. %OH = IOH x M(OH) x 100 / (M(KOH) x 1000)

[0533] Example 2: preparation of an adhesive composition

[0534] 2.1. Preparation of the -NCO component

[0535] In a closed 1 L reactor, equipped with stirring, heating means and a thermometer, 332.52 g of LUPRANAT MIPS (corresponding to a number of -NCO functions equal to 2.658 mmol / g) and 667.43 g of the composition of example 1 (corresponding to an equivalent number of -OH functions equal to 0.880 mmol / g) are introduced under a flow of nitrogen and at room temperature.

[0536] The quantities introduced by weight thus correspond to an equivalent NCO₃ / OH molar ratio of 3.02 (see Table 2). The mixture is maintained at 80 °C for 3 hours until complete consumption of the hydroxyl groups of the polyols in the composition of Example 1, corresponding to an -NCO₃ content (monitored by potentiometric titration) of 7.46 w / w (see Table 2). Then, 0.05 g of phosphoric acid (85% solution) is added and the mixture is stirred for 30 minutes.

[0537] 1000 g of polyurethane is obtained, corresponding to an equivalent number of -NCO functions of 1.777 mmol / g.

[0538] 2.2. Preparation of the adhesive composition

[0539] Castor oil from VERTELLUS is used as the -OH component.

[0540] The -NCO component prepared in § 2.1 is mixed with the -OH component in a ratio of one equivalent molar ratio -NCO / -OH equal to 1.74, which by weight corresponds to a mixture of 100 g of compound -NCO for 35 g of component -OH (taking into account the weight content of the -NCO group of the component -NCO prepared in § 2.1).

[0541] The mixing is carried out at a temperature between 35 and 50°C, to adjust the initial viscosity to around 1000 mPa·s, in the feed tank of the Nordmeccanica-type complexing machine. The Brookfield viscosity of the resulting composition is measured: the value obtained is shown in Table 2.

[0542] Examples 3 and 4: preparation of adhesive compositions

[0543] Preparation of the -NCO component:

[0544] For each composition G1 in Table 1, the protocol of the previous examples is repeated, adjusting the quantities of reactants so as to obtain the equivalent molar ratio NCO / OH indicated in Table 2.

[0545] The weight content of the -NCO group of the -NCO component obtained is indicated in Table 2. Preparation of the -OH component

[0546] The -OH component of examples 3 and 4 is identical to that of example 2. It is therefore 100% VERTELLUS castor oil. Preparation of the adhesive composition:

[0547] The protocol of Example 2 is repeated for the preparation of the adhesive compositions, maintaining a molar equivalent ratio of -NCO component / -OH component between 1.6 and 1.75, and calculating the corresponding weight quantities taking into account the weight content of the -NCO group of the -NCO component indicated in Table 2.

[0548] The results obtained are summarized in Table 2. Table 2: Adhesive compositions

[0549] [Tables2] Ex. 2 Ex. 3 Ex. 4 Composition G1 (Content by % weight) Example 1 100% - - Polyol Polyricin GR-50 - 100% - Polyol Polyricin GR-80 - - 100% Component -NCO Equivalent molar ratio NCO / OH 3.02 3.12 2.89 Content by group -NCO (% by weight) 7.48 5.89 7.47 Mixture of components -NCO and -OH Brookfield viscosity (mPa.s) 1113 (at 35°C) 1125 (at 50°C) 968 (at 50°C) NCO / OH molar ratio 1.74 1.65 1.60 Example 5: Preparation of a multilayer film

[0550] We are preparing a film consisting of:

[0551] - of a first oriented polyethylene film (MDOPE) with a thickness of 40 µm (TOTAL Lumicene Supertough);

[0552] - of an adhesive layer between the two films, from example 2;

[0553] - of a second polyethylene (LDPE) film with a thickness of 50 µm (Lotrène® FE8004).

[0554] This film is obtained by a sequential process by feeding the vat of a Nordmeccanica-type laminating machine with the adhesive composition of Example 2. This laminating machine is equipped with a roller-type coating device with an open vat, operating at a temperature between 35 and 50°C and at a speed of 50 m / minute. The adhesive layer bonding the two films at each interface has a thickness of approximately 2 µm, corresponding to approximately 2 g / m² of adhesive composition.

[0555] The adhesive layer is cross-linked after several days. Infrared analysis is performed on the adhesive to verify the disappearance of the NCO absorption band. Example 6: Mechanical recycling process, Step 1 of grinding

[0556] The multilayer complex of Example 5 PE / adhesive / PE is ground using an MDS 340 / 150 shredder with an 8 mm die to obtain chips. These are dried for 24 hours at 80°C in a dryer. The moisture content is controlled and must be less than 1% before the mixing phase in a MAS co-rotating twin-screw conical extruder with pressure indicator and melt screen.

[0557] This grinding step leads to a mixture of chips. Granulation stage 2

[0558] Step 2 consists of granulating the mixture obtained in step 1. This step is carried out in an Accrapak Systems BMI5 granulation machine, well-known in the field. The chips are fed into the machine, melted at a temperature above their melting point, and extruded. At the end of this step, granules are obtained with dimensions of approximately 3 mm in length and 2 mm in cross-section (measured, for example, with calipers or a ruler). Example 7: Preparation of single-layer films

[0559] The granules obtained in example 6 are mixed with Borealis FT5230 polyethylene granules (called virgin, i.e. not having been initially recycled) in a mass ratio of example 6 granules / virgin PE granules ranging from 1 / 99 to 100 / 0 (see table 3).

[0560] The single-layer films are manufactured on a blown coextrusion line with a single-screw extruder.

[0561] The process parameters are adjusted to manufacture single-layer films comprising a layer of a thickness indicated in Table 3.

[0562] Among the parameters usually set, we can mention: - Film extruder temperatures between 160°C and 230°C, - The inflation ratio (BUR: Blow Up Ratio) used is between 2.1 and 3.8.

[0563] The process typically comprises:

[0564] (i) the introduction, into the extruder, of the aforementioned mixture of granules,

[0565] (ii) the transformation by heating said granules into a viscous liquid state, then

[0566] (iii) the passage of the flux through an extrusion head comprising a coplanar and concentric annular die heated to a temperature of 230°C, so as to form a tubular bubble,

[0567] (iv) the radial expansion (relative to the plane of the annular spinnerets) and the stretching (in the direction perpendicular to said plane) of the bubble, then

[0568] (v) the cooling of said bubble.

[0569] The bubble is then flattened by the rollers, cut at the edges to separate the two layers. The films formed are rewound for storage.

[0570] Example 8: properties of the films obtained in example 7

[0571] The properties of the different films prepared are described in Tables 3, 4 and 5 following. Mechanical properties

[0572] The stresses at break and elongation at break are determined according to the method described in ISO 527-3 (specimen dimensions 33x6 mm2; tensile speed 50mm / min; 7 measurements taken for each reference).

[0573] Table 3: Mechanical properties

[0574] [Tables3] Example Recycled Granules from Example 6 Virgin PE Granules (FT5230) Film Thickness Achieved (microns) Tensile Strength (MPa) Elongation at Break (%) 8.1 (control) 0% 100% 43 + 3 31 + 9 545 + 120 8.2 25% 75% 43 + 2 23 + 9 532 + 262 8.3 50% 50% 41 + 5 30 + 3 589 + 60 8.4 75% 25% 35 + 3 30 + 7 573 + 158

[0575] Films comprising 25% to 75% by weight of recycled granules (films 8.2, 8.3 and 8.4) advantageously lead to stresses at break similar to that obtained for the reference film (control 8.1) which does not contain recycled granules of example 6. The same applies to elongation at break.

[0576] Films 8.2, 8.3 and 8.4 advantageously lead to good mechanical properties, at least almost identical to a film devoid of recycled materials (control 8.1). Film Characterizations

[0577] The following spectroscopic measurements were performed using a KONICA MINOLTA CM5 spectrocolorimeter. These measurements were carried out on samples of the films listed in Table 3 with an observation angle of 10° and a D65 light source. The following properties were measured using this spectrocolorimeter: haze (ASTM D1003-97), brightness (ISO 2470), transparency (Y), and saturation (C*). In addition, luminance / lightness (L*) and yellow (b*) were measured in the CieLab color space, which is a coordinate system of opposite colors, also obtained using the spectrocolorimeter. The results are summarized in Table 4 below.

[0578] The measurements are taken in white or in black (which corresponds in table 4 to the measurement environment).

[0579] Table 4: Film characterizations

[0580] [Tables4] Example Recycled Granules from Example 6 Virgin PE Granules (FT5230) C* (saturation) b* (yellow) Haze (cloudiness) Brightness SS (bleaching / brightness) L* (luminosity / clarity) Y (transparency) Measurement Environment - - white white white black black black 8.1 (control) 0% 100% 0.24 0.23 8.75% 10.61% 35.36 8.68% 8.2 25% 75% 0.17 0.17 7.29% 9% 32.48 7.3% 8.3 50% 50% 0.24 0.24 10.22% 12.1% 37.88 10.02% 8.4 75% 25% 0.24 0.24 11.2% 13.18% 39.47 10.94%

[0581] Table 4 demonstrates that films 8.2, 8.3, and 8.4 advantageously have very similar characteristics: saturation C*, yellow b*, haze, gloss, clarity L*, and transparency. These properties make them suitable recycled films for various applications, such as food packaging.

[0582] The delta Haze and delta L* values ​​were measured and are shown in Table 5 below. The delta values ​​are calculated from the values ​​of the films according to the invention relative to each of the reference films (control 8.1).

[0583] Table 5: Film characterizations in relation to control 8.1

[0584] [Tables5] Example Recycled Pellets from Example 6 Virgin PE Pellets (FT5230) Delta haze (turbidity) (absolute value) Delta L* (absolute value) Measurement Environment - - white black 8.1 (control) 0% 100% 0% 0 8.2 25% 75% 1.46% 2.88 8.3 50% 50% 1.47% 2.12 8.4 75% 25% 2.45% 4.11

[0585] Table 5 demonstrates that films 8.2, 8.3, and 8.4 advantageously exhibit a delta Haze and a delta L* (in the given measurement environment) of less than 5% (respectively less than 5), and even more preferably less than 3% (respectively less than 3), compared to the reference film (control 8.1). Thus, the Haze and L* results are very close to the values ​​obtained with the reference film (control 8.1).

[0586] In addition, the appearance of the films was evaluated, in particular to check for the formation of (unmelted) gels. These observations were made visually at 30 cm from the sample. The results are summarized in Table 6 below.

[0587] Table 6: Appearance of films

[0588] [Tableauxô] Example Recycled Granules from Example 6 Virgin PE Granules (FT5230) Gel Observation 8.1 (control) 0% 100% No 8.2 25% 75% No 8.3 50% 50% No 8.4 75% 25% No

[0589] Advantageously, films 8.2, 8.3 and 8.4, which respectively comprise 25%, 50% to 75% of recycled granules, do not show any (unmelted) gels by visual observation, which attests to a good quality of the films obtained.

Claims

1. Demands Use of a multilayer Fl system comprising: - a Cl layer comprising at least one polyolefin, - an adhesive layer A comprising the reaction product between an -NCO component and an -OH component, - a C2 layer comprising at least one polyolefin, to prepare a recycled article, said multilayer system Fl comprising at least 90% by weight of a polyolefin or a mixture of polyolefins relative to the total weight of said system, characterized in that the adhesive layer A is obtained from an adhesive composition CA comprising an -OH component and an -NCO component such as: - the -OH component is a composition comprising at least one Al polyol; - the component -NCO is a composition comprising at least one polyurethane obtained by polyaddition reaction from a composition G2 comprising at least one polyisocyanate, and a composition G1 comprising at least one polyol A2, said adhesive composition CA being characterized in that at least one of the polyols Al or A2 is selected from the following polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), and mixtures thereof: [Chem. 45] (I) (III-3) (IV-3) (V) (VI) in which: - R° is a hydrogen, an ethyl or a methyl; - R1 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R1 possibly comprising one or more heteroatoms selected from oxygen and sulfur; - R2 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R2 possibly comprising one or more heteroatoms selected from oxygen and sulfur; - Ra is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; - Rb is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; - x is an integer representing 0 or 1; - y is an integer representing 0 or 1 - z is an integer ranging from 1 to 9; - s is an integer ranging from 0 to 6; - t is an integer ranging from 1 to 4; - f is an integer equal to 2 or 3; - f' is an integer equal to 2 or 3; - f and g are integers such as the molecular mass the number (Mn) of the compound of formula (I) ranges from 600 to 20,000 g / mol; - f' and g' are integers such that the number molecular mass (Mn) of the compound of formula (II) ranges from 600 to 20,000 g / mol; R3 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; R4 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R5 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; R6 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; Each carbon-carbon bond, denoted by , represents either a single bond or a double bond. each / X' bond means that the bond is geometrically oriented to one side or the other with respect to the double bond (cis (Z) or trans (E)); n1 is an integer such that the number molecular mass (Mn) of the compound of formula (III-1) ranges from 1000 to 20,000 g / mol; n2 is an integer such that the number molecular mass (Mn) of the compound of formula (III-2) ranges from 1000 to 20,000 g / mol; n3 is an integer such that the number molecular mass (Mn) of the compound of formula (III-3) ranges from 1000 to 20,000 g / mol; m1 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-1) ranges from 1000 to 20,000 g / mol; m2 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-2) ranges from 1000 to 20,000 g / mol; m3 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-3) ranges from 1000 to 20,000 g / mol; p is an integer such that the number molecular mass (Mn) of the compound of formula (V) ranges from 1000 to 20,000 g / mol; u is an integer such that the number molecular mass (Mn) of the compound of formula (VI) ranges from 1,000 to 20,000 g / mol; Rc is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms;

2. - Rd is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; or Rc and Rd together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles possibly being substituted by one or more saturated or unsaturated alkyl groups; - Re is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rf is a saturated linear alkyl radical comprising 6 to 8 carbon atoms; - R" is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rh is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; or R" and Rh together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles possibly being substituted by one or more saturated or unsaturated alkyl groups; - R' is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Ri is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rk is a saturated linear alkyl radical, comprising 6 to 10 carbon atoms; characterized in that each of the Cl and C2 layers comprises, independently of each other, a polyolefin selected from polyethylene (PE), polypropylene (PP), ethylene-propylene copolymers, and mixtures thereof, preferably a polyolefin selected from PE, PP, and mixtures thereof. Use according to claim 1, characterized in that each of the Cl and C2 layers, independently of each other, comprises more than 90% by weight of a polyolefin (or a mixture of polyolefins), more preferably more than 95% by weight, and even more preferably more than 99% by weight of a polyolefin (or a mixture of polyolefins) relative to the total weight of said Cl layer (or C2 respectively).

3. Use according to any one of claims 1 to 2, characterized in that: - layer Cl comprises at least one polyethylene and layer C2 comprises at least one polyethylene, or - one of the layers Cl or C2 comprises at least one polypropylene, and the other layer comprises at least one polyethylene, or - layer C2 comprises at least one polypropylene and layer C2 comprises at least one polypropylene.

4. Use according to any one of claims 1 to 3, characterized in that R1 is a divalent or trivalent aliphatic radical, saturated or unsaturated, comprising from 2 to 60 carbon atoms, R1 preferably being an alkylene radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms, even more advantageously from 2 to 20 carbon atoms.

5. Use according to any one of claims 1 to 4, characterized in that composition G1 comprises at least one polyol A2 selected from polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), and mixtures thereof, preferably composition G1 comprises one polyol A2 selected from those of formula (I).

6. Use according to any one of claims 1 to 5, characterized in that the polyols of formula (I) are those of formula (IA) or (IB) following: [Chem.46] r oi ro ihj . .. ... o î o} ns r ¢-¾ w ' Ra -¼ (IA)

7. (IB) with x, y, z, g, Ra, R1, and being such as defined in claim 1, and preferably those of formula (IA1) or (IA-2): [Chem. 47] (IAl) (IA-2) in which R1, x, y, z, g, and / H' are as defined in any one of claims 5 or 6, v is an integer representing 0 or 1, and w is an integer from 0 to 10, preferably from 0 to 5, the polyols of formula (I) being more preferably polyols of formula (IAl). Use according to any one of claims 1 to 6, characterized in that the polyol of formula (I) is: [Chem.48]

8. in which g and R1 are as defined in claim 1, R1 preferably being a branched propylene. Use according to any one of claims 1 to 7, characterized in that the Al polyol is selected from: - a polyol of formula (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) or (VI) as defined according to any one of claims 1 to 7, - a hydroxylated triglyceride type polyol extracted from natural or genetically modified plant materials (e.g. castor, camelina, palm, legume, lesquerella, brassica or brassicacea), - a polyol obtained from the hydroxylation of unsaturated vegetable oils, - a polyol obtained from the hydroxymethylation of unsaturated vegetable oils, or - mixtures thereof, polyol A1 being preferably a hydroxylated triglyceride type polyol obtained from naturally hydroxylated vegetable oil.

9. Use according to any one of claims 1 to 8, characterized in that the multilayer system Fl comprises at least 92%, preferably at least 95% by weight, and even more preferably at least 97% by weight of polyolefin or a mixture of polyolefins relative to the total weight of said system.

10. Use according to any one of claims 1 to 9, characterized in that the recycled article comprises a recycled material content greater than or equal to 10%, more preferably greater than or equal to 25%, and more advantageously greater than or equal to 50%.

11. A mechanical recycling process for a multilayer system Fl as defined according to any one of claims 1 to 10, said process comprising: - i) a step of supplying the multilayer system Fl, and - ii) a step of grinding said multilayer system Fl.

12. A process according to claim 11, characterized in that it further comprises a washing step iii-1) of the chips obtained at the end of step ii), an optional flotation step iii-2), and a drying step iii-

13. □y Process according to claim 11 or 12, characterized in that it further comprises an extrusion / granulation step v) to obtain granules.

14. A process according to claim 13, characterized in that it further comprises a step of mixing a-2) the granules obtained in step v) with virgin PO polyolefin granules.

15. A process according to any one of claims 13 or 14, characterized in that the granule composition obtained at the end of step v) or a-2) comprises a polyolefin and a reaction product between an -NCO component and an -OH component, in a content less than or equal to 5% by weight, preferably less than or equal to 3%, and even more preferably less than or equal to 2.5% by weight relative to the total weight of said composition.

16. A process according to any one of claims 13 to 15, characterized in that it comprises a step of shaping vi) the pellet composition obtained in step v) or a-2) into a recycled article.

17. Use of a CA adhesive composition comprising: - an -OH component which is a composition comprising at least one Al polyol; - an -NCO component which is a composition comprising at least one polyurethane obtained by polyaddition reaction from a G2 composition comprising at least one polyisocyanate, and a G1 composition comprising at least one A2 polyol, at least one of the Al or A2 polyols being selected from the following polyols of formulas (I), (II), (III-1), (III-2), (III-3), (IV-1), (IV-2), (IV-3), (V) and (VI), and mixtures thereof: [Chem.49] (II) (III-D (IV-1) (IV-2) (IV-3) (V) (VI) in which: - R° is a hydrogen, an ethyl or a methyl; - R1 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R1 possibly comprising one or more heteroatoms selected from oxygen and sulfur; - R2 is a divalent or trivalent hydrocarbon radical, saturated or unsaturated, linear or branched, comprising from 2 to 60 carbon atoms, said radical R2 possibly comprising one or more heteroatoms selected from oxygen and sulfur; - Ra is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; - Rb is an alkyl radical, saturated or unsaturated, preferably linear, comprising 5 to 14 carbon atoms; - x is an integer representing 0 or 1; - y is an integer representing 0 or 1 - z is an integer ranging from 1 to 9; - s is an integer ranging from 0 to 6; - t is an integer ranging from 1 to 4; - f is an integer equal to 2 or 3; - f' is an integer equal to 2 or 3; - f and g are integers such as the molecular mass the number (Mn) of the compound of formula (I) ranges from 600 to 20,000 g / mol; - f' and g' are integers such that the number molecular mass (Mn) of the compound of formula (II) ranges from 600 to 20,000 g / mol; - R3 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; - R4 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; - R5 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 1 to 38 carbon atoms; - R6 is a divalent hydrocarbon radical, saturated or unsaturated, comprising from 2 to 40 carbon atoms; - Each carbon-carbon bond, denoted by , represents either a single bond or a double bond. - each bond means that the bond is geometrically oriented to one side or the other with respect to the double bond (cis (Z) or trans (E)); - n1 is an integer such that the number molecular mass (Mn) of the compound of formula (III-1) ranges from 1000 to 20,000 g / mol; - n2 is an integer such that the number molecular mass (Mn) of the compound of formula (III-2) ranges from 1000 to 20,000 g / mol; - n3 is an integer such that the number molecular mass (Mn) of the compound of formula (III-3) ranges from 1000 to 20,000 g / mol; - m1 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-1) ranges from 1000 to 20,000 g / mol; - m2 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-2) ranges from 1000 to 20,000 g / mol; - m3 is an integer such that the number molecular mass (Mn) of the compound of formula (IV-3) ranges from 1000 to 20,000 g / mol; - p is an integer such that the number molecular mass (Mn) of the compound of formula (V) ranges from 1000 to 20,000 g / mol; - u is an integer such that the number molecular mass (Mn) of the compound of formula (VI) ranges from 1,000 to 20,000 g / mol; - Rc is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rd is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; or Rc and Rd together form a non-aromatic, saturated or unsaturated cycle or bicycle, or an aromatic cycle, said cycles or bicycles possibly being substituted by one or more saturated or unsaturated alkyl groups; - Re is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rf is a saturated linear alkyl radical comprising 6 to 8 carbon atoms; - R" is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; - Rh is a linear alkyl radical, saturated or unsaturated, comprising 8 to 10 carbon atoms; or R" and Rh together form a non-aromatic, saturated or unsaturated ring or bicycle, or an aromatic ring, said rings or bicycles possibly being substituted by one or more saturated or unsaturated alkyl groups; - R' is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Ri is a saturated linear alkyl radical, comprising 6 to 8 carbon atoms; - Rk is a saturated linear alkyl radical, comprising 6 to 10 carbon atoms; to prepare a recycled article.

18. Use according to claim 17, characterized in that the recycled article comprises a recycled material content greater than or equal to 10%, more preferably greater than or equal to 25%, and more advantageously greater than or equal to 50%.