Compositions comprising polyester and modified softwood lignin

Abstract

The present invention discloses a composition that can be extruded and / or injection molded, comprising chemically modified softwood lignin and a polyester selected from PBS (polybutylene succinate), PBAT (polybutylene adipate terephthalate), and PCL (polycaprolactone), or a mixture thereof. The chemically modified softwood lignin comprises 10 to 25 weight percent of the total weight of the composition.

Description

Technical Field

[0001] The present invention relates to a composition comprising polyester and chemically modified softwood lignin. The composition can be injection molded. Background Art

[0002] More renewable plastic materials are needed, and lignin is a potential natural polymer to be used.

[0003] Lignin is the most readily available natural polymer after cellulose. Along with cellulose and hemicellulose, lignin is present in the cell walls of fibrous plants and wood. Lignin serves as the matrix material for polysaccharides, microfibrils, and fibers, and provides strength to plant stems. It is a high-molecular-weight phenolic macromolecule composed of three different types of monolignols: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

[0004] In recent years, have paid a lot of efforts to develop new plastic material, these plastic materials are the mixture of well-known synthetic polymers, such as for example polyolefin, polyester and polynitrile, and various forms of xylogen.So, the consumer goods part that for example is made of such mixture is made of xylogen.Therefore, compared with the corresponding product that is made of synthetic polymer as unique main component, they can be considered to be more environmentally friendly, and synthetic polymer is derived from non-recyclable fossil source usually.The problem that this type of mixture will overcome comprises that the overall miscibility of xylogen and various synthetic polymers is relatively low, and the thermal stability of tight xylogen is relatively low, and the undesirable characteristic of gained mixture, for example relatively low toughness, fracture strain or tensile strength.Paid effort to solve such problem by modification xylogen used, for example by adjusting production parameters and by producing back chemical modification.

[0005] Polyester is a natural or synthetic polymer composed of repeating units linked by ester groups (-OC[=O]-). Examples of thermoplastic synthetic polyesters include polybutylene adipate terephthalate (PBAT), used, for example, as a biodegradable alternative to polyethylene in plastic bags; and polybutylene succinate (PBS), often the material of choice for biodegradable plastic films. Further examples of thermoplastic polyesters include polylactic acid (PLA), used, for example, as a material for plastic filaments, polycaprolactone (PCL), which can be used, for example, as an impact-reinforcing additive, and polybutylene terephthalate (PBT), often used, for example, as an electrical insulator.

[0006] WO2018 / 111183 A1 discloses a polymer material comprising a first polymer and modified lignin. It teaches that the first polymer can be a natural or synthetic polymer. Separate embodiments related to the first polymer include a polymer selected from the group consisting of polyolefins, polyesters, and polynitriles. Disadvantages of this type of polymer material include a significant reduction in tensile strength and elongation at break compared to the first polymer alone.

[0007] In the Journal of the American Association of Pulp and Paper Engineers (Tappi Journal), March 2017, Vol. 3, pp. 111-121, Glasser et al. disclose compostable films comprising a biodegradable polyester and modified kraft lignin. The modified kraft lignin is obtained by O-alkylating the corresponding lignin using propylene oxide as an alkylating agent. Disadvantages of this type of compostable film include unstable bubbles during melt processing of 12-14 μm films when the modified kraft lignin content exceeds 30%.

[0008] US 9,000,075 B2 discloses a composition comprising a reaction product obtained by a transesterification reaction between hydroxypropyl lignin and a polyester. Disadvantages of such compositions include the need for special conditions, such as the use of a catalyst, suitable for forming a covalent bond at a stage in the manufacturing process when the hydroxypropyl lignin and the polyester are in close proximity. Summary of the Invention

[0009] The present invention discloses one or several solutions on how to overcome one or several disadvantages of the above-mentioned prior art.

[0010] It is an object of the present invention to provide a composition comprising modified lignin, wherein the composition can be processed using conventional techniques such as extrusion, kneading, film blowing and injection molding.

[0011] Another object of the present invention is to disclose a composition comprising modified lignin and polyester, which composition has such physical properties that products made therefrom can be used as substitutes for corresponding products made only from polyester.

[0012] Yet another object of the present invention is to disclose a composition comprising modified lignin and polyester, the composition having a toughness and / or strain at break comparable to or exceeding the corresponding toughness and / or strain at break of the polyester itself.

[0013] In a first aspect, the present invention relates to a composition comprising chemically modified softwood lignin and a polyester, wherein the chemically modified softwood lignin carries one or several O-substituents of formulae IS to VI-S.

[0014]

[0015] Thus, the hydroxyl groups of the softwood lignin are substituted and thus carry, via covalent bonds, one or more substituents of formulae 1S to VI-S, indicated by dashed lines, derived from the hydroxyl oxygen atoms of the softwood lignin. The substituent R comprises at least 4 carbon atoms, and the polyester is one or more of PLA, PCL, PBT, PEF, PHA, PHB, PBS, and PBAT. The chemically modified softwood lignin represents 2 to 45% by weight of the total weight of the composition.

[0016] In a second aspect, the invention relates to a product which comprises the composition and which can be extruded and / or injection moulded.

[0017] In a third aspect, the present invention relates to a method of extruding a composition, comprising the steps of: mixing chemically modified softwood lignin and a polyester and optionally a compatibilizer to form a mixture; extruding the mixture at a temperature of at least 100°C to form an extruded material; optionally cutting the extruded material into pellets; and optionally drying the extruded material.

[0018] In a fourth aspect, the present invention relates to a method of injection molding a composition, the method comprising the steps of: providing pellets or powder of the composition; and injection molding the pellets or powder into a desired shape at a temperature of at least 100°C.

[0019] All embodiments herein are applicable in all respects. DETAILED DESCRIPTION

[0020] In this application, the term "lignin" means a polymer comprising coumarin, coniferyl and sinapyl alcohol monomers.

[0021] In this application, the terms "linker" or "linker group" are used interchangeably and refer to any group that can link lignin to a chemical group (e.g., a chemical group comprising an alkyl or alkylene fragment). It should be understood that a portion of the linker (e.g., an oxygen atom) can be derived from lignin and, after a precursor (e.g., a synthetic intermediate) is attached to the lignin, forms part of the linker itself.

[0022] In this application, the term "compatibilizer" means a compound that promotes adhesion between polymers that are otherwise poorly compatible. Compatibilizers are widely used to increase the miscibility of originally immiscible polymers or polymers that do not mix so well.

[0023] In the present application, the term "softwood lignin" (SWL) is understood as lignin derived from softwood, ie wood from gymnosperm trees.

[0024] The botanical distinction between softwoods and hardwoods lies in their reproduction, not their end use or appearance. All trees reproduce by producing seeds, but the seed structure differs. Generally speaking, hardwoods come from deciduous trees that shed their leaves annually, while softwoods come from coniferous trees that generally remain evergreen. Hardwoods tend to grow slower and, therefore, are generally denser. Softwood trees are known as gymnosperms. Gymnosperms reproduce by forming cones, which release pollen that is carried by the wind to other trees. Hardwoods are angiosperms, a type of plant that produces seeds or fruits with some kind of covering, such as a shell.

[0025] Examples of softwood trees include, but are not limited to, trees of the genus Araucaria, such as hoop pine (Araucaria cunninghamii), monkey puzzle tree (Araucaria araucana), and paraná pine (Araucaria angustifolia), trees of the genus Cedrus, such as atlas cedar (Cedrus atlantica), cyprus cedar (Cedrus brevifolia), Himalayan cedar (Cedrus deodara), Lebanon cedar (Cedrus libani), northern white cedar (Thuja occidentalis), Atlantic white cedar (Chamaecyparis thyoides), eastern red cedar (Juniperus virginiana), and western red cedar (Thuja plicata), trees of the Cupressaceae family, for example, Arizona cypress (Cupressus arizonica), southern cypress (Taxodium distichum), Chilean cypress (Fitzroya cupressoides), hinoki cypress (Chamaecyparis obtusa), lawson's cypress (Chamaecyparis lawsoniana), Mediterranean cypress (Cupressus sempervirens), nootk cypress (Cupressus nootkatensis), coast redwood (Sequoia sempervirens), Japanese cedar (Cryptomeria japonica), and rimu (Dacrydium cupressinum), trees of the genus Douglas-fir,For example, coast douglas-fir (Pseudotsuga menziesii var. menziesii) and rocky mountain douglas-fir (Pseudotsuga menziesii var. glauca), trees of the Taxaceae family, such as the European yew (Taxus baccata), trees of the genus Abies, such as the balsam fir (Abies balsamea), silver fir (Abies alba), noble fir (Abies procera), and pacific silver fir (Abies amabilis), trees of the genus Hemlock, such as the eastern hemlock (Tsuga canadensis), mountain hemlock (Tsuga mertensiana), western hemlock (Tsuga heterophylla), Huon cypress (Tsuga truncatum), and cypress. pine), macquarie pine (Lagarostrobos franklinii), kauri (Agathis australis), Queensland kauri (Agathis robusta), Japanese nutmeg-yew and kaya (Torreya nucifera), trees of the genus larch, such as the European larch (Larix decidua), the Japanese larch (Larix kaempferi), the North American larch (Larix laricina), and the western larch (Larix occidentalis), trees of the genus pine,Examples include European black pine (Pinus nigra), jack pine (Pinus banksiana), lodgepole pine (Pinus contorta), monterey pine (Pinus radiata), ponderosa pine (Pinus ponderosa), red pine (Pinus resinosa), eastern white pine (Pinus strobus), western white pine (Pinus monticola), sugar pine (Pinus lambertiana), loblolly pine (Pinus taeda), longleaf pine (Pinus palustris), pitch pine (Pinus rigida), and shortleaf pine (Pinus echinata), as well as trees of the genus Picea, such as the norway spruce (Picea abies), black spruce (Picea mariana), red spruce (Picea rubens), sitka spruce (Picea sitchensis), and white spruce (Picea glauca).

[0026] In the present application, the term "softwood kraft lignin" (SWKL) is to be understood as a subset of SWL, wherein SWKL is produced by withdrawing black liquor from the kraft process and precipitating the lignin by lowering the pH, as is familiar to the skilled person, for example according to the Lignoboost process, the SLRP process or the LignoForce process.

[0027] In the present application, the term "softwood organosolv lignin" (SWOL) is understood to be a subset of SWL, wherein SWOL is produced by extracting lignin and hemicellulose from wood with the aid of an organic solvent, such as, for example, acetone, methanol, ethanol, butanol, ethylene glycol, formic acid or acetic acid, as is well known to the skilled person. The wood can be pretreated with an alkali, acid or enzyme (cellulase). The lignin can be separated from the solvent and hemicellulose by precipitation, for example, by adding water and sometimes also by simultaneously lowering the pH.

[0028] In the present application, the term "softwood soda pulp lignin" (SWSPL) is to be understood as a subset of SWL, wherein SWSPL is produced by precipitation of black liquor from an alkaline pulping process and lowering the pH, e.g. according to the Lignoboost process, the SLRP process or the LignoForce process, as is well known to the skilled person.

[0029] Lignin

[0030] Lignin useful in producing the compositions of the present invention may be obtained from any suitable form of softwood, such as, for example, sawdust or wood chips. An illustration of a lignin including the text "LIG" is depicted below (hydroxyl groups not shown).

[0031]

[0032] Softwoods are preferred for their high lignin content. The Kappa number estimates the amount of chemicals required during pulp bleaching to achieve a pulp with a given brightness. Because the amount of bleaching agent required is related to the lignin content in the pulp, the Kappa number can be used to monitor the effectiveness of the lignin extraction stage in the pulping process. It is roughly proportional to the residual lignin content of the pulp.

[0033] K≈c*l

[0034] K: Kappa number; c: constant ≈6.57 (depending on the method and wood); l: lignin content, expressed as a percentage. The Kappa number is determined according to ISO 302:2004. The Kappa number may be 20 or higher, 40 or higher, or 60 or higher. In one embodiment, the Kappa number is from 10 to 100.

[0035] The softwood material can be a mixture of softwood materials, and in one embodiment, the softwood material is black liquor or red liquor, or a material obtained from black liquor or red liquor. Black liquor and red liquor contain cellulose, hemicellulose and lignin and derivatives thereof. The SWL that can be used to produce the composition of the present invention can include black liquor or red liquor, or lignin obtained from black liquor or red liquor.

[0036] Black liquor consists of four main organic components: approximately 30-45% by weight of woody material, 25-35% by weight of saccharinic acid, approximately 10% by weight of formic and acetic acid, 3-5% by weight of extractives, approximately 1% by weight of methanol, and various inorganic elements and sulfur. The exact composition of the liquor varies and depends on the cooking conditions and the raw materials used in the production process. Red liquor includes ions from the sulfite process (calcium, sodium, magnesium, or ammonium), sulfonated lignin, hemicellulose, and low-molecular-weight resins.

[0037] The lignin that can be used to produce the composition of the present invention is essentially SWL, such as, for example, SWKL. In one embodiment, the lignin can be a SWL selected from the group of SWL consisting of: SWKL, SWOL and SWSPL. In one embodiment, the lignin can be a SWL selected from the group of SWL consisting of: In another embodiment, the lignin can be SWKL. In another embodiment, the lignin can be an organosolv lignin. The lignin can be in the form of particles having a particle size of 5 mm or less or 1 mm or less.

[0038] Native lignin or kraft lignin is insoluble in most organic solvents, fatty acids or oils. Instead, the prior art has proposed various techniques to depolymerize and convert the depolymerized lignin into components that are soluble in the desired medium.

[0039] The weight average molecular weight (mass) (M) of the lignin that can be used to produce the composition of the present invention w ) can be 30,000 g / mol or less, such as no more than 20,000 g / mol, or no more than 10,000 g / mol, or no more than 5,000 g / mol, or no more than 2,000 g / mol, but is preferably higher than 1,000 g / mol, or higher than 1,200 g / mol, or higher than 1,500 g / mol. In one embodiment, the number average molecular weight of the lignin is between 1,000 and 4,000 g / mol, or between 1,500 and 3,500 g / mol.

[0040] Modified or derivatized lignin

[0041] The lignin that can be used to produce the composition of the present invention is essentially modified or derivatized with a chemical group R comprising at least 4 carbon atoms. The group R can be, but is not limited to, an alkyl group such as, for example, C 10 -C 20 -alkyl or C 12 -C 17 -alkyl; an aryl group such as phenyl; or -(CH2CH2O) nCH2CH2Oalk, wherein n is 1 to 180 and alk is H, methyl or ethyl.Group R can be saturated, unsaturated, straight chain, branched, cyclic, and it can be further substituted by little substituent, such as for example OH, NH2, COOH, COO-alkyl or methyl.Group R is basically connected to lignin by the linking group L comprising 0 to 3 carbon atoms, 1 to 3 oxygen atoms and 0 to 1 nitrogen-atoms.Linking group L can be derived from the hydroxyl group of lignin.Therefore, linking group L can comprise oxygen atoms, which can usually derive from original lignin.According to schematic chemical structures 1 and 2, linking group L can be connected to the aryl group or the aliphatic moiety on the lignin:

[0042]

[0043] In Formulas 1 and 2 above, lignin is schematically represented by R" and an aromatic or aliphatic group, respectively, L is a linker and R is a chemical group mentioned and explained herein. Since lignin has an aliphatic hydroxyl group and an aromatic hydroxyl group, the linker L can be connected to the aliphatic portion of the lignin (Structure 2). The linker L can also be directly connected to the aromatic group in the lignin (Structure 1). R" can be a hydrogen, an alkyl, an aromatic or an alkoxy group or any other group found in lignin. The aromatic group of the lignin can include more than one R".

[0044] The degree of modification of the hydroxyl group of the lignin that can be used for producing composition of the present invention can be expressed as the equivalent number of lignin repeating unit.Equivalent number can be 0.01 or higher, 0.05 or higher, 0.1 or higher, 0.2 or higher, or 0.4 or higher, or 0.6 or higher or 0.8 or higher.In this application, it is assumed that the repeating unit of lignin has a molecular weight of 180g / mol.When lignin was chemically modified, the degree of modification of lignin can be very low and still miscible with the first polymer.In one embodiment, equivalent number can be 0.01-0.2, such as 0.05-0.2 or 0.1-0.15.

[0045] The lignin that can be used to produce the composition of the invention is essentially SWL, such as for example SWKL, SWOL or SWSPL.

[0046] According to one embodiment, linking group L can be the chemical group including 3 carbon atoms and 3 oxygen atoms.For example, lignin (such as SWKL, SWOL or SWSPL) can be with the group R being connected to lignin by alkylene glycol linking key, i.e.-OCH described as formula I 2CH (OH) CH 2O-group or-OCH described as formula II 2CH (CH 2OH) O-group modification.The linking group L of modified lignin can be replaced by O- by group R at one of oxygen atom.The oxygen atom of linking group L (being bonded to the lignin in modified lignin or its part) can be derived from original lignin, i.e. the lignin before any modification producing modified lignin. Alternatively, the oxygen atom of linking group L (being bonded to the lignin in modified lignin or its part) can be derived from chemical reactant, and linking group L is formed by this chemical reactant by the chemical reaction with lignin.

[0047]

[0048] The modified lignin of formula I or II can be produced or synthesized as described below by the reaction between the compound according to formula SM2 and lignin (hydroxyl groups are not shown). According to the compound of formula SM2, it can be directly synthesized by reacting the compound according to formula SM1 with epichlorohydrin, or alternatively, by the corresponding epoxide ring-opening product, then the intramolecular reformation of epoxide by displacement intermediate chloride is synthesized, as known in the art and described below. According to the compound of formula SM2, it can also be synthesized by the O-allylation of the compound of formula SM1, for example, with allyl bromide, then oxidized, for example, with peracid, as known in the art. When producing or synthesizing the modified lignin of formula I or II of the present invention, according to the compound of formula SM2, in situ generation can be carried out under the existence of lignin.

[0049]

[0050] The R group of the modified SWL of formula I or formula II according to the present invention can be a straight chain, cyclic, branched, saturated or unsaturated alkyl group including 4 to 36 carbon atoms, such as, for example, 4 to 25, 14 to 18, 12 to 15 or 12 to 14 carbon atoms. The R group of the modified SWL of formula I or formula II according to the present invention can be independently selected from the group consisting of: saturated alkyl, unsaturated alkyl, straight chain alkyl, branched chain alkyl and cyclic alkyl. Such an alkyl group can be further substituted by a substituent independently selected from the group consisting of: -OH, -NH2, -COOH, aryl and phenyl. Such an alkyl group can be further combined with one or more fragments selected from the group of fragments, the group being selected from -COO-, -S- and -O-. The R group of the modified SWL of formula I or formula II according to the present invention can be independently selected from the group consisting of: phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl and nonylphenyl. The R groups of the modified SWL of formula I or formula II according to the present invention can be independently selected from the group consisting of compounds of formula S1, S2, S3, S4, S5 and S6 as depicted below. The integer n of the compounds of formula S1, S2, S3, S4, S5 and S6 can be 1-180, 1-100, 1-50, 1-25, 1-10, 1-5 or 1-2.

[0051]

[0052] The R groups of the modified SWL of formula I or formula II according to the present invention may include a plurality of different R groups. For example, such modified lignin may be prepared as taught herein by reacting 2 to 20% (such as 6%) of cresyl glycidyl ether and 2 to 15% (such as 6%) of C 12 -C 14 - prepared by reaction of glycidyl ether.

[0053] According to one embodiment, linking group L can include 1 carbon atom, a nitrogen atom and 2 oxygen atoms, such as for example when it is a carbamate group.For example, lignin (such as SWKL, SWOL or SWSPL) can be modified with the group R that is connected to lignin by the carbamate moiety, i.e. -NHC(=O)O- group as described in formula III. The oxygen atom of linking group L (bonded to the lignin in the modified lignin or a part thereof) can be derived from original lignin, i.e. the lignin before any modification that produces the modified lignin. Alternatively, the oxygen atom of linking group L (bonded to the lignin in the modified lignin or a part thereof) can be derived from a chemical reactant, and linking group L is formed by the chemical reactant by a chemical reaction with lignin.

[0054]

[0055] Modified lignin of formula III can be produced or synthesized as depicted below by reaction between isocyanate according to formula SM3 and lignin (hydroxyl groups not shown). US3072634(A) discloses a detailed description example of the synthesis of compounds according to formula III.

[0056]

[0057] The R groups of the modified SWL of formula III according to the present invention can be linear, cyclic, branched, saturated or unsaturated alkyl groups, benzyl and phenyl, and the alkyl group includes 4 to 36 carbon atoms, such as, for example, 4 to 25, 14 to 18, 12 to 15 or 12 to 14 carbon atoms. Such R groups can be further substituted by substituents independently selected from the group consisting of: aryl, phenyl and ester. Such R groups can be further combined with one or more fragments selected from the group of fragments, the group being selected from -COO-, -S- and -O-. The R groups of the modified SWL of formula III according to the present invention can be independently selected from the group consisting of: phenyl, cyclohexyl and octadecyl. The R groups of the modified SWL of formula III according to the present invention can be independently selected from the group consisting of: compounds of formula S1, S2, S3, S4, S5 and S6 as described above. The integer n of the compounds of Formula S1, S2, S3, S4, S5 and S6 can be 1-180, 1-100, 1-50, 1-25, 1-10, 1-5 or 1-2.

[0058] The R groups of the modified SWL of Formula III according to the present invention can include a plurality of different R groups. Such a plurality can be selected from two, three or more R groups from the list consisting of: saturated alkyl, unsaturated alkyl, linear alkyl, branched alkyl and cyclic alkyl. The alkyl group can be further substituted with a substituent independently selected from the group consisting of: aryl, phenyl and epoxide. The alkyl group can be combined with one or more fragments selected from the group of fragments selected from -COO-, -S- and -O-.

[0059] According to one embodiment, linking group L can be an oxygen atom.For example, lignin (such as SWKL, SWOL or SWSPL) can be modified with the group R that is connected to lignin by an oxygen atom, i.e., the -O- group described as formula IV. The oxygen atom of linking group L (bonded to the lignin in the modified lignin or a part thereof) can be derived from original lignin, i.e., the lignin before any modification that produces the modified lignin. Alternatively, the oxygen atom of linking group L (bonded to the lignin in the modified lignin or a part thereof) can be derived from a chemical reactant, and linking group L is formed by the chemical reactant with the chemical reaction of lignin.

[0060]

[0061] Modified lignin of formula IV can be produced or synthesized as depicted below by the reaction between an electrophile according to formula SM4 carrying a leaving group X, such as chloride, bromide, mesylate, etc., and lignin (hydroxyl groups not shown). The synthesis of compounds of formula IV is disclosed in Ind. Eng. Chem. Res. 2012, 51, 51, 16713-16720.

[0062]

[0063] The R group of the modified SWL of formula IV according to the present invention can be a straight chain, cyclic, branched, saturated or unsaturated alkyl group comprising 4 to 36 carbon atoms, such as, for example, 4 to 25, 14 to 18, 12 to 15 or 12 to 14 carbon atoms. The R group of the modified SWL of formula IV according to the present invention can be a saturated alkyl group, an unsaturated alkyl group, a straight chain alkyl group, a branched chain alkyl group and a cyclic alkyl group. Such R groups can be further substituted by substituents independently selected from the group consisting of: -OH, -NH2, -COOH, an aryl group and a phenyl group. Such R groups can be further combined with one or more fragments selected from the group of fragments, the group being selected from -COO-, -S- and -O-. The R group of the modified SWL of formula IV according to the present invention can be independently selected from the group consisting of: benzyl, o-methylbenzyl, p-methylbenzyl, cyclohexyl, 4-tert-butylbenzyl, 2-ethylhexyl and nonylphenyl. The R groups of the modified SWL of formula IV according to the present invention can be independently selected from the group consisting of compounds of formula S1, S2, S3, S4, S5 and S6 as described above. The integer n of the compounds of formula S1, S2, S3, S4, S5 and S6 can be 1-180, 1-100, 1-50, 1-25, 1-10, 1-5 or 1-2.

[0064] The R groups of the modified SWL of formula IV according to the present invention can include a plurality of different R groups. Such a plurality can be selected from two, three or more R groups selected from the list consisting of: saturated alkyl, unsaturated alkyl, linear alkyl, branched alkyl and cyclic alkyl. The alkyl group can be further substituted with a substituent independently selected from the group consisting of: aryl, phenyl, benzyl and allyl. The alkyl group can be combined with one or more fragments selected from the group consisting of -COO-, -S- and -O-.

[0065] According to one embodiment, the linking group L can include 1 carbon atom and two oxygen atoms, such as, for example, when it is an ester group. For example, lignin (such as SWKL, SWOL or SWSPL) can be modified with a group R that is connected to the lignin through an ester moiety, i.e., a -C(=O)O- group as depicted in Formula V. The oxygen atom of the linking group L (bonded to the lignin or a portion thereof in the modified lignin) can be derived from the original lignin, i.e., the lignin before any modification that produces the modified lignin. Alternatively, the oxygen atom of the linking group L (bonded to the lignin or a portion thereof in the modified lignin) can be derived from a chemical reactant, and the linking group L is formed by the chemical reactant by a chemical reaction with the lignin.

[0066]

[0067] The modified lignin of formula V can be produced or synthesized by the reaction between a compound according to formula SM5, SM6 or SM7 and lignin (hydroxyl groups not shown) as depicted below. In US2016355535A, it is taught how to synthesize a compound according to formula V from the corresponding lignin.

[0068]

[0069] The R group of the modified SWL of formula V according to the present invention can be a linear, cyclic, branched, saturated or unsaturated alkyl group comprising 4 to 36 carbon atoms, such as, for example, 4 to 25, 14 to 18, 12 to 15 or 12 to 14 carbon atoms. The R group of the modified SWL of formula V according to the present invention can be a saturated alkyl group, an unsaturated alkyl group, a linear alkyl group, a branched alkyl group and a cyclic alkyl group. Such an alkyl group can be further substituted by a substituent independently selected from the group consisting of: -OH, -NH2, -COOH, an aryl group, a phenyl group, a benzyl group and an allyl group. Such an R group can be further substituted by a substituent independently selected from the group consisting of: an aryl group and a phenyl group. Such an R group can be further combined with one or more fragments selected from the group consisting of -COO-, -S- and -O-. The R group of the modified SWL of formula V according to the present invention can be independently selected from the group consisting of: phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, octadecyl and benzyl. The R groups of the modified SWL of formula V according to the present invention can be independently selected from the group consisting of compounds of formula S1, S2, S3, S4, S5 and S6 as described above. The integer n of the compounds of formula S1, S2, S3, S4, S5 and S6 can be 1-180, 1-100, 1-50, 1-25, 1-10, 1-5 or 1-2.

[0070] The R groups of the modified SWL of formula V according to the present invention may include a plurality of different R groups. Such a plurality may be selected from two, three or more R groups selected from the list consisting of: saturated alkyl, unsaturated alkyl, linear alkyl, branched alkyl and cyclic alkyl. The alkyl group may be further substituted with a substituent independently selected from the group consisting of: aryl, phenyl, benzyl and allyl. The alkyl group may be combined with one or more fragments selected from the group consisting of -COO-, -S- and -O.

[0071] According to one embodiment, linking group L can include 2 carbon atoms and an oxygen atom, such as for example when it is a dimethylsiloxy group.For example, lignin (such as SWKL, SWOL or SWSPL) can be used with the group R being connected to lignin by dimethylsiloxy moiety, i.e. -Si (Me) 2O- group modification as described in formula VI. The oxygen atom of linking group L (being bonded to the lignin in the modified lignin or its part) can be derived from original lignin, i.e. the lignin before any modification producing the modified lignin. Alternatively, the oxygen atom of linking group L (being bonded to the lignin in the modified lignin or its part) can be derived from chemical reactant, and linking group L is formed by the chemical reactant with the chemical reaction of lignin.

[0072]

[0073] Modified lignin of formula VI can be produced or synthesized by reacting a compound according to formula SM8 (wherein X can be a halogen, such as, for example, Cl) with lignin (hydroxyl groups not shown) as depicted below. In ACS Sustainable Chem. Eng. 2016, 4, 10, 5212-5222, it is taught how compounds of formula VI can be synthesized from the corresponding lignin.

[0074]

[0075] The R group of the modified SWL of formula VI according to the present invention can be a linear, cyclic, branched, saturated or unsaturated alkyl group comprising 4 to 36 carbon atoms, such as, for example, 4 to 25, 14 to 18, 12 to 15 or 12 to 14 carbon atoms. The R group of the modified SWL of formula VI according to the present invention can be a saturated alkyl group, an unsaturated alkyl group, a linear alkyl group, a branched alkyl group and a cyclic alkyl group. Such an alkyl group can be further substituted by a substituent independently selected from the group consisting of: an aryl group, a phenyl group, a benzyl group and an allyl group. Such an R group can be further substituted by a substituent independently selected from the group consisting of: an aryl group and a phenyl group. Such an R group can be further combined with one or more fragments selected from the group consisting of -COO-, -S- and -O-. The R group of the modified SWL of formula VI according to the present invention can be independently selected from the group consisting of: a phenyl group, an o-methylphenyl group, a p-methylphenyl group, a tert-butyl group, a methyl group, a cyclohexyl group, a 4-tert-butylphenyl group, a 2-ethylhexyl group, an octadecyl group, a dodecyl group and a benzyl group. The R groups of the modified SWL of formula VI according to the present invention can be independently selected from the group consisting of compounds of formula S1, S2, S3, S4, S5 and S6 as described above. The integer n of the compounds of formula S1, S2, S3, S4, S5 and S6 can be 1-180, 1-100, 1-50, 1-25, 1-10, 1-5 or 1-2.

[0076] The R groups of the modified SWL of formula VI according to the present invention can include a plurality of different R groups. Such a plurality can be selected from two, three or more R groups from the list consisting of: saturated alkyl, unsaturated alkyl, straight chain alkyl, branched chain alkyl and cyclic alkyl. The alkyl group can be further substituted by a substituent independently selected from the group consisting of: aryl, phenyl, benzyl and allyl. The alkyl group can be combined with one or more fragments selected from the group of fragments, the group being selected from -COO-, -S- and -O-.

[0077] Composition according to the present invention can be by first preparing by linking group L with group R modification or derivatized lignin, then the modified lignin is mixed with polyester to prepare, this polyester is such as for example PET, PBAT, PLA, PCL, PBT, polyethylene 2,5-furandicarboxylate (PEF), polyhydroxyalkanoate (PHA), polyhydroxybutyrate (PHB) or PBS.Can be modified in a suitable solvent.Modified lignin can be separated from the modified reaction mixture, or when mixing with polyester such as for example PBAT, PLA, PCL, PBT, PEF, PHA, PHB or PBS, modified lignin can be stayed in the reaction mixture.Can be mixed by stirring or shaking or in any other suitable manner, and then can heat slurry.Any suitable technology can be used to remove any catalyst and any other undesirable component afterwards.

[0078] The composition according to the invention may alternatively be prepared by reacting lignin with a suitable reagent to link groups R via linkers L as taught herein while mixed with a polyester such as, for example, PBAT, PLA, PCL, PBT, PEF, PHA, PHB or PBS.

[0079] The chemical modification of lignin (e.g., SWL or SWKL) can be carried out at 60°C and 250°C, such as 60°C or higher, 80°C or higher, or 100°C or higher, or 120°C or higher, or 150°C or higher, or 160°C or higher, or 180°C or higher, but preferably not higher than 250°C.

[0080] Compositions comprising chemically modified SWL and polyester

[0081] The present invention relates to a composition comprising a polyester and a chemically modified SWL. The composition is essentially a mixture of a polyester (e.g., PLA, PCL, PBT, PEF, PHA, PHB, PBS, or PBAT) and a chemically modified SWL (e.g., SWKL, according to Figures I, II, III, IV, V, VI, or mixtures thereof). Modification to produce the modified SWL can be accomplished by reacting the SWL with a suitable reagent as taught elsewhere herein.

[0082] Surprisingly, it has been found that the compositions of the present invention have one or several advantageous physicochemical properties, such as, for example, tensile strength, film-forming properties, such as, for example, film-forming properties of less than or equal to 20 μm or 12 μm, and elongation at break, compared to the corresponding pure polyester itself or to the corresponding compositions of the prior art. According to the current prior art, as further detailed herein above, one or several such physicochemical properties of mixtures of chemically modified lignin and polyester would be expected to be less advantageous compared to the corresponding pure polyester.

[0083] The optimal range of chemically modified SWL in the composition of the present invention can be 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% of the composition of the present invention.

[0084] In the composition of the present invention, the polyester may generally constitute substantially the remainder of the total weight of the composition, after deducting the weight of the chemically modified SWL. The sum of the single or multiple polyesters and the single or multiple chemically modified SWL may constitute more than 90 wt-%, such as more than 95, 98 or 99 wt-%, of the total weight of the composition. The remaining 10, 5, 2 and 1 wt-%, respectively, may be constituted by one or more suitable fillers, compatibilizers, etc.

[0085] Advantageous physicochemical properties of the compositions of the present invention may include, but are not limited to, one or more of the group consisting of: strain at break, Young's modulus, film-forming properties, and toughness.

[0086] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a mixture of compounds according to formula I and II, wherein the polyester is selected from the group consisting of PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT. The substituent R of formula I and II may be selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cashew, nonylphenyl and compounds of formula S1, S2, S3, S4, S5 and S6, wherein the integer m can be 3 to 10 and the integer n can be 1 to 180. The composition can include 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0087] According to one embodiment, the composition of the present invention may include a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula III, wherein the polyester is selected from the group consisting of PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT. The substituent R of formula III may be selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cashew, nonylphenyl and compounds of formula S1, S2, S3, S4, S5 and S6, wherein the integer m can be 3 to 10 and the integer n can be 1 to 180. The composition can include 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0088] According to one embodiment, the composition of the present invention may include a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula IV, and the polyester is selected from the group consisting of: PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT. The substituent R of formula IV may be selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cashew, nonylphenyl and compounds of formula S1, S2, S3, S4, S5 and S6, wherein the integer m can be 3 to 10 and the integer n can be 1 to 180. The composition can include 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0089] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula V, wherein the polyester is selected from the group consisting of PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT. The substituent R of formula V may be selected from C4-C 25%. The composition may comprise 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0090] According to one embodiment, the composition of the present invention may include a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula VI, and the polyester is selected from the group consisting of: PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT. The substituent R of formula VI may be selected from C4-C 25 %. The composition may comprise 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0091] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula I, II or IV, and the polyester is selected from the group consisting of polyesters: PBS and PBAT. The substituent R of the compound according to formula I, II or IV may be selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cashew, nonylphenyl and compounds of formula S1, S2, S3, S4, S5 and S6, wherein the integer m can be 3 to 10 and the integer n can be 1 to 180. The composition can include 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0092] According to one embodiment, the composition of the present invention may include a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula I, II or IV, and the polyester is selected from the group consisting of polyesters: PBS, PBAT and PCL. The substituent R of the compound according to formula I, II or IV may be selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cashew alkyl, nonylphenyl, wherein the integer m can be 3 to 10. The composition can include 10 to 25 weight-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0093] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula IV, wherein the polyester is selected from the group consisting of polyesters: PBS and PBAT. The substituent R of the compound according to formula IV may be selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl and CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, wherein the integer m can be from 3 to 10. The composition can include 10 to 25 weight-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0094] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula I and / or II and the polyester is PCL. The substituent R of the compound according to formula I and / or II may be selected from C4-C 25 -alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl, nonylphenyl, such as selected from C4-C 25 -alkyl and o-methylphenyl. The composition may comprise 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0095] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula I or II or a mixture thereof, wherein the polyester is selected from the group consisting of polyesters: PBS and PBAT. The substituent R of the compound according to formula I or II may be selected from C4-C 25 %. The composition may comprise 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such a composition include improved strain at break compared to the polyester itself.

[0096] According to one embodiment, the composition of the present invention may comprise a chemically modified SWL and a polyester, wherein the chemically modified SWL is a compound according to formula IV, wherein the polyester is selected from the group consisting of polyesters: PBS and PBAT. The substituent R of the compound according to formula IV may be selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl and CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 alkyl, wherein the integer m can be from 3 to 10. The composition can include 2 to 45 wt-%, such as 2 to 40 wt-%, 2 to 35 wt-%, such as 5 to 30 wt-%, 5 to 25 wt-%, 10 to 35 wt-%, 10 to 30 wt-% or 10 to 25 wt-% SWL. Advantages of such compositions include improved strain at break compared to the polyester itself.

[0097] Studies have shown that the compositions of the present invention can be processed by extrusion and injection molding even without the addition of any compatibilizer. The modified SWL can be blended with polyester and then extruded at a sufficiently high temperature, such as above 100°C, for example, 110-250°C, 130-240°C, 140-220°C, 140-200°C, 140-190°C, or 140-180°C. Extrusion can be performed using a twin-screw extruder. The resulting extruded product can be pelletized or powdered, which can then be dried using any suitable technique.

[0098] Injection molding of the present composition can also be performed at temperatures above 100°C, such as above 110°C or even at 200°C or higher, without any increase in viscosity or pressure. In one embodiment, the temperature is 110-250°C. The starting material for injection molding can be pellets or powders obtained by extrusion as described above. Injection molding is advantageous in that more complex shapes and structures can be produced from existing materials.

[0099] According to one embodiment, the composition of the present invention can be extruded or injection molded to obtain a physical product. Such a physical product can have a predetermined shape, depending on its production and well understood by the skilled person. Such a physical product can be produced by extruding the first polymer further described herein, the modified lignin of the present invention, and optionally a compatibilizer to form a mixture. The mixture can be extruded at a temperature of at least 100° C., preferably at least 170° C. or at least 250° C., to form an extruded material. The extruded material can then be optionally cut before drying.

[0100] According to one embodiment, the composition of the present invention can be injection molded. For example, powder or pellets of the composition can be molded into a desired shape at a temperature of at least 100°C, or preferably at least 180°C or at least 250°C.

[0101] According to one embodiment, the modified SWL of the present invention may be thermally stable at temperatures up to 150°C, or up to 180°C, or up to 200°C, or up to 220°C, or up to 240°C.

[0102] According to one embodiment, the modified SWL of the present invention can be used as the sole component or one of the components of a compatibilizer. For example, the modified SWL can be mixed with a polymer or polymer mixture in solution, dry state or melt.

[0103] Example

[0104] Material

[0105] The lignin (SWKL) used in this example was derived from spruce black liquor from the kraft process, where the lignin was precipitated using the Ligno Boost method and then dried to produce lignin powder. C12-C14-glycidyl ether oil (Cas# 68609-97-2) was purchased from AL.PAS GmbH. 9,10-Epoxyoctadecanoic acid methyl ester oil was produced in-house by peroxidation of methyl oleate (90% purity) purchased from Chemtronica AB (Sweden).

[0106] Preparation of chemically modified SWL (Examples 1:1 to 1:3:2)

[0107] Example 1:1 Preparation of a mixture of chemically modified SWKL consisting of a compound according to formula IV (wherein R is CH[(CH2)7CH3]CH(OH)(CH2)7C(=O)OCH3) and a compound according to formula IV (wherein R is CH[CH(OH)(CH2)7CH3](CH2)7C(=O)OCH3) by reaction in an extruder, wherein a premixed lignin-oil mixture was used

[0108] Extruder: LabTech twin-screw extruder; screw diameter = 20 mm, L / D = 48; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 that build up pressure to the die; motor power = 5.5 kW.

[0109] Before feeding the extruder, 2.64 kg of lignin powder (4% moisture) and 360 g (0.086 mol eq.) of 9,10-epoxyoctadecanoic acid methyl ester oil (epoxidized fatty acid methyl ester; epoxy FAME) were premixed. The screw speed was set to 90 rpm. Processing temperatures were set as follows: unheated feed barrel section, 80°C for the second barrel section, 150°C for the third barrel section, 170°C for the fourth barrel section, 190°C for the fifth through twelfth barrel sections, and 175°C for the die. A 400 mbar vacuum was applied to barrel section 11 to remove moisture and volatiles. Two black, viscous strands were collected from the die.

[0110] Example 1:2:1: Preparation of chemically modified SWKL according to formula I and II by reaction in an extruder, wherein R is C 12 -C 14 -alkyl.

[0111] Extruder: LabTech twin-screw extruder; screw diameter = 20 mm, L / D = 60; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW

[0112] Before feeding into the extruder, 2.64 kg of lignin powder and 360 g (0.033 moleq.) of C 12 -C 14-Glycidyl ether oil premix. The screw speed was set to 350 rpm. Processing temperatures were set as follows: 80°C in the first barrel section equipped with a side feeder (lignin oil feed), 80°C in the second barrel section, 150°C in the third barrel section, 170°C in the fourth barrel section, and 190°C in the fifth, fifth, and fifteenth barrels and the die section. The tenth barrel was equipped with an atmospheric vent. A 400 mbar vacuum was applied to barrel section 14 to remove moisture and volatiles. Two black, viscous strands were collected from the die.

[0113] Example 1:2:2: Preparation of chemically modified SWKL according to formula I and II by reaction in an extruder, wherein R is C 12 -C 14 -alkyl.

[0114] Extruder: LabTech twin-screw extruder; screw diameter = 20 mm, L / D = 60; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW

[0115] Before feeding into the extruder, 2.4 kg of lignin powder and 600 g (0.058 moleq.) of C 12 -C 14 -Glycidyl ether oil premix. The screw speed was set to 350 rpm. Processing temperatures were set as follows: 80°C (lignin feed) in the first barrel section equipped with a side feeder, 80°C (oil feed) in the second barrel section equipped with a liquid metering port, 150°C (3rd barrel section), 170°C (4th barrel section), and 190°C (5th through 15th barrel sections and die sections). The tenth barrel was equipped with an atmospheric vent. A 400 mbar vacuum was applied to barrel section 14 to remove moisture and volatiles. Two black, viscous strands were collected from the die.

[0116] Example 1:3:1: Preparation of chemically modified SWKL according to formula I and II, wherein R is o-tolyl, by reaction in an extruder, wherein a premixed lignin-oil mixture is used

[0117] Extruder: LabTech twin-screw extruder; screw diameter = 20 mm, L / D = 60; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW

[0118] 2.64 kg of lignin powder and 360 g (0.156 mol eq.) of O-cresyl glycidyl ether oil were premixed before feeding into the extruder. The screw speed was set to 350 rpm. The processing temperature was set as follows: unheated feed barrel sections, 80°C for the first barrel section equipped with a side feeder (lignin feed), 80°C for the second barrel section equipped with a liquid metering port (oil feed), 150°C for the third barrel section, 170°C for the fourth barrel section, and 190°C for the fifth to fifteenth barrels and the die section. The tenth barrel was equipped with an atmospheric vent. A vacuum of 400 mbar was applied to barrel section 14 to remove moisture and volatiles. Two black, viscous strands were collected from the die.

[0119] Example 1:3:2: Preparation of chemically modified SWKL according to formula I and II, wherein R is o-methylphenyl, i.e. o-tolyl, by reaction in an extruder, wherein a premixed lignin-oil mixture is used

[0120] Extruder: LabTech twin-screw extruder; screw diameter = 20 mm, L / D = 60; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW

[0121] 2.4 kg of lignin powder and 600 g (0.274 mol eq.) of O-cresyl glycidyl ether oil were premixed before feeding into the extruder. The screw speed was set to 350 rpm. The processing temperature was set as follows: unheated feed barrel sections, 80°C for the first barrel section equipped with a side feeder (lignin feed), 80°C for the second barrel section equipped with a liquid metering port (oil feed), 150°C for the third barrel section, 170°C for the fourth barrel section, and 190°C for the fifth to fifteenth barrels and the die section. The tenth barrel was equipped with an atmospheric vent. A vacuum of 400 mbar was applied to barrel section 14 to remove moisture and volatiles. Two black, viscous strands were collected from the die.

[0122] Production of compositions comprising chemically modified SWL and polyester (Examples 2:1 to 2:13)

[0123] Example 2:1 Production of a composition comprising 10 wt.-% of a chemically modified SWKL according to formula IV and 90 wt.-% of a polyester that is PBS

[0124] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 10 wt.% of the modified lignin from Example 1:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: the feed barrel section was unheated, the first barrel section was 80°C, the second barrel section was 150°C, the third to eleventh barrel sections were 170°C, and the die was 180°C. Both strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0125] Example 2:2 Production of a composition comprising 25 wt.-% of a chemically modified SWKL according to formula IV and 75 wt.-% of a polyester that is PBS

[0126] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 25 wt.% of the modified lignin from Example 1:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: the feed barrel section was unheated, the first barrel section was 80°C, the second barrel section was 150°C, the third to eleventh barrel sections were 170°C, and the die was 180°C. Both strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0127] Example 2:3 Production of a composition comprising 50 wt.-% of a chemically modified SWKL according to formula IV and 50 wt.-% of a polyester that is PBS

[0128] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 50 wt.% of the modified lignin from Example 1:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: the feed barrel section was unheated, the first barrel section was 80°C, the second barrel section was 150°C, the third to eleventh barrel sections were 170°C, and the die was 180°C. Both strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0129] Example 2: Production of Reference Materials of 4 Polyester PBS

[0130] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; screw profile with conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: unheated feed barrel section, 80°C for the first barrel section, 150°C for the second barrel section, 170°C for the third to eleventh barrel sections, and 180°C for the die. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0131] Example 2:5 Production of a composition comprising 10 wt.-% of a chemically modified SWKL according to formula IV and 90 wt.-% of a polyester that is PBAT

[0132] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM003) was blended with 10 wt.% of the modified lignin from Example 1:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: the feed barrel section was unheated, the first barrel section was 80°C, the second barrel section was 150°C, the third to eleventh barrel sections were 170°C, and the die was 180°C. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0133] Example 2:6 Production of a composition comprising 40 wt.-% of a chemically modified SWKL according to formula IV and 60 wt.-% of a polyester that is PBAT

[0134] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 40 wt.% of the modified lignin from Example 1:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the material was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: the feed barrel section was unheated, the first barrel section was 80°C, the second barrel section was 150°C, the third to eleventh barrel sections were 170°C, and the die was 180°C. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0135] Example 2: Production of a Reference Material of Polyester PBAT

[0136] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM003) were blended in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 48; motor power = 5.5 kW; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 10, and conveying elements from barrels 11-12 to build up pressure to the die). The total feed rate of the materials was set to 3 kg / h, and the screw speed was set to 90 rpm. The processing temperature was set as follows: unheated feed barrel section, 80°C for the first barrel section, 150°C for the second barrel section, 170°C for the third to eleventh barrel sections, and 180°C for the die. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0137] Example 2:8 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:2:1 and 75 wt.-% of a polyester that is PBAT

[0138] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 25 wt.% of the modified lignin from Example 1:2:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the material was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) for the first barrel section equipped with a side feeder, 150°C for the second-third barrel sections, and 190°C for the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0139] Example 2:8:1 Production of a composition comprising 25 wt-% of the chemically modified SWKL according to formulas I and II from Example 1:2:2 and 75 wt-% of a polyester that is PBAT

[0140] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 25 wt.% of the modified lignin from Example 1:2:2 using the same machine, settings and procedure as in Example 2:8.

[0141] Example 2:8:2 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:3:1 and 75 wt.-% of a polyester that is PBAT

[0142] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 25 wt.% of modified lignin from Example 1:3:1 using the same machine, settings and procedure as in Example 2:8.

[0143] Example 2:9 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:3:2 and 75 wt.-% of a polyester that is PBAT

[0144] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 25 wt.% of the modified lignin from Example 1:3:2 using the same machine, settings and procedure as in Example 2:8.

[0145] Example 2:10 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulae I and II from Example 1:2:1 and 75 wt.-% of a polyester that is PBS

[0146] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 25 wt.% of the modified lignin from Example 1:2:1 using the same machine, settings and procedure as in Example 2:8.

[0147] Example 2:11 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:2:2 and 75 wt.-% of a polyester that is PBS

[0148] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 25 wt.% of the modified lignin from Example 1:2:2 using the same machine, settings and procedure as in Example 2:8.

[0149] Example 2:12 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:3:1 and 75 wt.-% of a polyester that is PBS

[0150] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 25 wt.% of the modified lignin from Example 1:3:1 using the same machine, settings and procedure as in Example 2:8.

[0151] Example 2:13 Production of a composition comprising 25 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:3:2 and 75 wt.-% of a polyester that is PBS

[0152] Polybutylene succinate (PBS) (BioPBSFD72PM from PTT MCC Biochem Company Ltd) was blended with 25 wt.% of the modified lignin from Example 1:3:2 using the same machine, settings and procedure as in Example 2:8.

[0153] Example 2:14 Production of a composition comprising 20 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:2:1 and 80 wt.-% of a polyester that is PBAT

[0154] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 20 wt.% of the modified lignin from Example 1:2:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the material was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) for the first barrel section equipped with a side feeder, 150°C for the second-third barrel sections, and 190°C for the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0155] Example 2:15 Production of a composition comprising 20 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:2:1 and 80 wt.-% of a polyester that is PCL

[0156] Polycaprolactone (PCL) (Ingevity TMCAPA 6500) was blended with 20 wt.% of the modified lignin from Example 1:2:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the materials was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) in the first barrel section equipped with a side feeder, 150°C in the second-third barrel sections, and 190°C in the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0157] Example 2:16 Production of a composition comprising 30 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:2:1 and 70 wt.-% of a polyester that is PCL

[0158] Polycaprolactone (PCL) (Ingevity TM CAPA 6500) was blended with 30 wt.% of the modified lignin from Example 1:2:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the materials was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) in the first barrel section equipped with a side feeder, 150°C in the second-third barrel sections, and 190°C in the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0159] Example 2: Production of a Reference Material of 17 Polyester PCL

[0160] Polycaprolactone (PCL) (Ingevity TMCAPA 6500) were blended in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the materials was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) in the first barrel section equipped with a side feeder, 150°C in the second-third barrel sections, and 190°C in the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0161] Example 2:18 Production of a composition comprising 20 wt.-% of the chemically modified SWKL according to formulas I and II from Example 1:3:1 and 80 wt.-% of a polyester that is PBAT

[0162] Polybutylene adipate terephthalate (PBAT) (Ecoworld TM 003) was blended with 20 wt.% of the modified lignin from Example 1:3:1 in a LabTech twin-screw extruder (screw diameter = 20 mm, L / D = 60; the screw profile had conveying elements from barrels 1-3, conveying and kneading elements from barrels 4 to 13, and conveying elements from barrels 14-15 to build up pressure to the die; motor power = 11 kW). The total feed rate of the material was set to 4 kg / h, and the screw speed was set to 350 rpm. The processing temperature was set as follows: 80°C (lignin feed) for the first barrel section equipped with a side feeder, 150°C for the second-third barrel sections, and 190°C for the fourth-fifteenth barrel and die sections. The two strands from the die were cooled on an air-cooled conveyor (2.6 m, 8 fans, wire mesh conveyor belt) and then pelletized in a strand pelletizer.

[0163] Physicochemical properties of the compositions of the present invention and comparison with corresponding polyesters

[0164] The pellets from Examples 2:1 to 2:7 and 2:14 to 2:18 were each melted into 15 g pucks. The pucks were pressed into films in a hot press. The hot press was equipped with a mold with a circular hole in the middle, 1 mm thick and 20 cm in diameter. The hot press was first heated to 165°C and then a pressure of 15 bar was applied for 10 seconds. The pressure was then increased to 50 bar for 10 seconds, and finally a pressure of 100 bar was applied for 30 seconds. Strips 15 mm wide were cut from the films.

[0165] The strips were conditioned overnight in a climate chamber at 23°C and 50% relative humidity (RH). Tensile testing was performed in the same climate chamber at the same temperature and RH. The test speed was set to 50 mm / min. The distance between the grips holding the strips on the machine was 50 mm.

[0166]

[0167] The results in the table above show that compositions comprising polyester and 10 or 25 wt-% of chemically modified SWL (Examples 2:1, 2:2 and 2:5 and 2:14, 2:15 and 2:18) unexpectedly have strain at break that exceeds that of the corresponding pure polyester (Examples 2:3 and 2:6 and 2:17).

[0168] Itemized list of implementation methods

[0169] 1. A composition comprising chemically modified softwood lignin and polyester, wherein:

[0170] - said chemically modified softwood lignin carries one or several O-substituents selected from the substituents of formulae IS to VI-S,

[0171]

[0172] -R comprises at least 4 carbon atoms;

[0173] - the polyester is one or more of PLA, PCL, PBT, PEF, PHA, PHB, PBS and PBAT; and

[0174] - the chemically modified softwood lignin represents 2 to 45 wt-% of the total weight of the composition.

[0175] 2. The composition according to claim 1, wherein

[0176] - the O-substituent is selected from the group consisting of substituents of formulae IS, II-S and IV-S; and

[0177] -R is independently selected from C4-C 25 -alkyl, CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl, nonylphenyl, and substituents of formula S1, S2, S3, S4, S5, and S6, wherein the integer m is 3 to 10 and the integer n is 1 to 180

[0178]

[0179] 3. The composition according to claim 2, wherein

[0180] - the O-substituent is a mixture of substituents of formula I and II or a substituent of formula IV;

[0181] - When the O-substituent is a mixture of substituents of formula IS and II-S, R is independently selected from C4-C 25 -alkyl, and substituents of formula S1, S2, S3, S4, S5 and S6, wherein the integer n is 1 to 180; and

[0182] - When the O-substituent is a substituent of formula IV-S, R is independently selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl groups and substituents of formula S1, S2, S3, S4, S5, and S6, wherein the integer m is 3 to 10 and the integer n is 1 to 180.

[0183] 4. The composition according to claim 3, wherein

[0184] - the O-substituent is a substituent of formula IV-S; and

[0185] -R is independently selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl and CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, wherein the integer m is 3 to 10.

[0186] 5. The composition of any one of the preceding claims, wherein the polyester is selected from PBS and PBAT or mixtures thereof.

[0187] 6. The composition according to any one of the preceding claims, wherein the chemically modified softwood lignin is derived from a softwood lignin selected from the group consisting of softwood kraft lignin (SWKL), softwood organosolv lignin (SWOL) and softwood soda pulp lignin (SWSPL).

[0188] 7. A composition according to any one of the preceding claims, wherein the chemically modified softwood lignin represents 2 to 35 wt-%, such as 10 to 25 wt-%, of the total weight of the composition, and the polyester represents substantially the remainder of the total weight of the composition.

[0189] 8. A product which is extruded and / or injection moulded and comprises the composition according to any one of claims 1 to 7.

[0190] 9. A method of extruding the composition according to any one of claims 1 to 7, comprising the steps of:

[0191] - mixing the chemically modified softwood lignin and the polyester and optionally a compatibilizer to form a mixture;

[0192] - extruding the mixture at a temperature of at least 100° C. to form an extruded material;

[0193] - optionally cutting the extruded material into pellets; and

[0194] - optionally drying the extruded material.

[0195] 10. A method of injection molding the composition according to any one of claims 1 to 7, comprising the steps of:

[0196] - providing granules or powder of the composition; and

[0197] - Injection moulding the pellets or powder into the desired shape at a temperature of at least 100°C.

Claims

1. A composition comprising chemically modified softwood lignin and polyester, wherein: - the chemically modified softwood lignin carries one or several O-substituents of formulae IS, II-S and IV-S; - When the O-substituent is selected from the substituents of formula IS and II-S or mixtures thereof, R is independently selected from C4-C 25 -alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl, nonylphenyl; and - When the O-substituent is a substituent of formula IV-S, R is independently selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 alkyl, CH[CH(OH)(CH2) m CH3](CH2) m C(=O)OC 1-3 Alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl, nonylphenyl, wherein the integer m is 3 to 10; and A) the polyester is selected from PBS (polybutylene succinate) and PBAT (polybutylene adipate terephthalate) and the chemically modified softwood lignin represents 2 to 35 wt-% of the total weight of the composition; or B) The polyester is PCL (polycaprolactone) and the chemically modified softwood lignin represents 10 to 25 wt-% of the total weight of the composition.

2. The composition according to claim 1, wherein - the chemically modified softwood lignin carries one or several O-substituents of formula IV-S; -R is independently selected from CH[(CH2) m CH3]CH(OH)(CH2) m C(=O)OC 1-3 Alkyl and CH[CH(OH)(CH2) m CH3](CH2)mC(=O)OC 1-3 Alkyl, wherein the integer m is 3 to 10; and - The polyester is selected from PBS (polybutylene succinate) and PBAT (polybutylene adipate terephthalate) or a mixture thereof.

3. The composition according to claim 1, wherein - the chemically modified softwood lignin carries one or several O-substituents of formulae IS and II-S, or mixtures thereof; -R is independently selected from C4-C 25 -alkyl, phenyl, o-methylphenyl, p-methylphenyl, cyclohexyl, 4-tert-butylphenyl, 2-ethylhexyl, cardanyl, nonylphenyl; and - The polyester is PCL (polycaprolactone).

4. The composition according to claim 3, wherein R is independently selected from C4-C 25 -alkyl and o-methylphenyl.

5. The composition according to any one of claims 1 to 4, wherein The chemically modified softwood lignin is derived from a softwood lignin selected from the group consisting of softwood kraft lignin (SWKL), softwood organosolv lignin (SWOL) and softwood soda pulp lignin (SWSPL).

6. A composition according to any one of the preceding claims, wherein Apart from the chemically modified softwood lignin, substantially the remainder of the total weight of the composition is the polyester.

7. A product which is extruded and / or injection moulded and comprises the composition according to any one of claims 1 to 6.

8. A method of extruding the composition according to any one of claims 1 to 6, comprising the steps of: - mixing the chemically modified softwood lignin and the polyester and optionally a compatibilizer to form a mixture; - extruding the mixture at a temperature of at least 100° C. to form an extruded material; - optionally cutting the extruded material into pellets; and - optionally drying the extruded material.

9. A method of injection molding the composition according to any one of claims 1 to 6, comprising the steps of: - providing granules or powder of the composition; and - Injection moulding the pellets or powder into the desired shape at a temperature of at least 100°C.

Images