Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B3/00—Preparation of cellulose esters of organic acids
  • C08B3/16—Preparation of mixed organic cellulose esters, e.g. cellulose aceto-formate or cellulose aceto-propionate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B3/00—Preparation of cellulose esters of organic acids
  • C08B3/20—Esterification with maintenance of the fibrous structure of the cellulose
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
  • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
  • C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
  • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
  • C08B37/14—Hemicellulose; Derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
  • C08L1/08—Cellulose derivatives
  • C08L1/10—Esters of organic acids, i.e. acylates
  • C08L1/14—Mixed esters, e.g. cellulose acetate-butyrate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
  • C08L5/14—Hemicellulose; Derivatives thereof
• • D—TEXTILES; PAPER
  • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
  • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
  • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
  • D21H17/03—Non-macromolecular organic compounds
  • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
  • D21H17/14—Carboxylic acids; Derivatives thereof

Definitions

• the present disclosure relates to a method for preparing esterified cellulose and/or hemicellulose , to an esterified cellulose and/or hemicellulose and to a thermoplastic cellulose and/or hemicellulose polymer material .
• Cellulose and hemicellulose are renewable raw materials well suited for producing thermoplastic materials .
• Cellulose and/or hemicellulose may be homogeneously esterified e . g . using ionic liquids or solvents such as DMAC-LiCl or TBAF-DMSO, but they may be toxic and challenging to recycle , thereby making them less desirable for sustainable production in an industrial scale .
• Heterogeneous esterification approaches may also involve the use of solvents , such as acetic acid, which may contribute significantly to waste generated by the esterification process .
• a method for preparing esterified cellulose and/or hemicellulose is disclosed .
• the method may comprise mixing an anhydride mixture and cellulose and/or hemicellulose , thereby obtaining an esterification mixture , such that the anhydride mixture esterifies the cellulose and/or hemicellulose at least partially, thereby forming the esterified cellulose and/or hemicellulose ; and wherein the anhydride mixture is obtainable or obtained by
• the initial anhydride mixture comprises a mixed anhydride having a fatty acyl group and a shortchain acyl group, a portion of the short-chain acid anhydride , a short-chain acid and optionally a fatty acid anhydride having two fatty acyl groups ;
• Fig . 1 schematically illustrates an embodiment of the esterification process .
• a method for preparing esterified cellulose and/or hemicellulose is disclosed .
• the method may comprise mixing an anhydride mixture and cellulose and/or hemicellulose , thereby obtaining an esterification mixture , such that the anhydride mixture esterifies the cellulose and/or hemicellulose at least partially, thereby forming the esterified cellulose and/or hemicellulose ; and wherein the anhydride mixture is obtainable or obtained by
• the initial anhydride mixture comprises a mixed anhydride having a fatty acyl group and a shortchain acyl group, at least a portion of the shortchain acid anhydride , a short-chain acid and optionally a fatty acid anhydride having two fatty acyl groups ;
• the reacting the fatty acid with the shortchain acid anhydride in the presence of the acid catalyst , such that the initial anhydride mixture is obtained, and the removing of the short-chain acid, the short-chain acid anhydride and optionally water and/or impurities present in the initial anhydride mixture at least partially from the initial anhydride mixture , thereby obtaining the anhydride mixture may be referred to as production of reactive fatty acids or production of the anhydride mixture in the context of this specification .
• the by-products of the production of the anhydride mixture (the short-chain acid and the short-chain acid anhydride ) may be removed from the initial anhydride mixture and reused in subsequent production of the anhydride mixture and/or valori zed as a product .
• the initial anhydride mixture obtained comprises a mixed anhydride ( acetic octanoic anhydride ) , a portion of the short-chain acid anhydride ( acetic anhydride ) that has not reacted, a short-chain acid ( acetic acid) , a fatty acid anhydride ( octanoic anhydride ) and a portion of the fatty acid ( octanoic acid) that has not reacted .
• acetic octanoic anhydride a mixed anhydride
• acetic anhydride a portion of the short-chain acid anhydride that has not reacted
• acetic acid acetic acid
• octanoic anhydride a fatty acid anhydride
• octanoic acid octanoic acid
• acetic acid and acetic anhydride may be removed or separated e.g. by vacuum distillation or by any other suitable method described in this specification to obtain the anhydride mixture that may be used for the esterification.
• distillation at a temperature of at least 140 °C may readily remove the acetic acid and acetic anhydride (and possibly also e.g. residual water) from the initial anhydride mixture, such that the acetic octanoic anhydride and the octanoic anhydride remain in the anhydride mixture.
• Scheme 2 shows an exemplary schematic of the reaction mechanism in the esterification. Although cellulose is depicted in the scheme, a skilled person will understand that similar reaction mechanisms may apply to hemicellulose or a mixture thereof .
• R alkyl of long chain faty acids
• the fatty acyls of the mixed anhydride may react with hydroxyl groups ( -OH) of the cellulose and/or hemicellulose , such that covalent ester bonds are formed .
• the short-chain acyls of the mixed anhydride ( and optionally of the short-chain acid anhydride ) may react with hydroxyl groups of the cellulose and/or hemicellulose .
• the removal of the short-chain acid and the short-chain acid anhydride at least partially from the initial anhydride mixture may increase the relative proportion of the mixed anhydride , a higher DS of the fatty acyl groups may be obtained than without it .
• thermoplastic cellulose and/or hemicellulose polymer material with desired properties , such as flowability and/or tensile strength .
• desired properties such as flowability and/or tensile strength .
• the need to add plastici zers to the thermoplastic cellulose and/or hemicellulose polymer material may be reduced .
• An extrudable thermoplastic cellulose and/or hemicellulose polymer material may also be obtained .
• the esterification may be performed as a one- pot reaction, i . e . in a single reactor .
• removing the short-chain acid, the short-chain acid anhydride and optionally water and/or impurities present in the initial anhydride mixture at least partially from the initial anhydride mixture , thereby obtaining the anhydride mixture may also be performed in a separate unit , for example in a separate distillation unit .
• the short-chain acid, short-chain acid anhydride , and/or the optional impurities may be at least partially removed by various different methods , including various separation and/or fractionation methods . This may enrich or increase the relative proportion of the mixed anhydride in the anhydride mixture . Thereby the degree of substitution of the fatty acyl ( s ) in the esterified cellulose and/or hemicellulose may be increased relative to the degree of substitution of the short-chain acyls .
• the impurities that may be at least partially removed may include e . g . possible degradation and/or side products of chemicals used in the method, and/or impurities from the chemicals used in the method .
• the short-chain acid, short-chain acid anhydride , and/or the optional impurities may have boiling points lower than the boiling points of the mixed anhydride and of the optional fatty acid anhydride .
• the short-chain acid, short-chain acid anhydride , and/or the optional impurities may be removed at least partially by a method capable of separating and/or fractionating compounds based on their boiling points . Examples of such methods may include e . g . distillation, vacuum distillation, and/or vacuum evaporation .
• the distillation may be performed at normal pressure ( ambient atmospheric pressure ) .
• Other methods that may be contemplated may include e . g .
• the short-chain acid, short-chain acid anhydride , and/or the optional impurities may be fractionated into two or more fractions .
• the proportion of the short-chain acid, short-chain acid anhydride , and/or the optional impurities that may be at least partially removed may depend e.g. on the proportion of the short-chain acid anhydride and other components in the initial anhydride mixture. For example, up to about 40 %
• short-chain acid may be understood as referring to a carboxylic acid having a shorter chain than the fatty acid(s) .
• short-chain acid anhydride may be understood as an anhydride of the short-chain acid, or of two short-chain acids, having a shorter chain than the fatty acid(s) .
• the short-chain acid anhydride may be represented by formula I wherein each Rx is independently selected from a C1-C4 alkyl.
• each R 1 may be the same (for example, both Rx groups in Formula I may be Cx alkyls, C2 alkyls, C3 alkyls or C4 alkyls) or they may be different. Each Rx may thus be independently selected from a Cx alkyl, a C2 alkyl, a C3 alkyl or a C4 alkyl.
• the mixed anhydride may be represented by formula II
• Rx is a C1-C4 alkyl
• R2 is an aliphatic chain having at least 4 carbon atoms, with the proviso that R 1 has fewer carbon atoms than R 2 .
• Rx may thus be selected from a Cx alkyl, a C2 alkyl, a C3 alkyl or a C4 alkyl .
• the optional fatty acid anhydride having two fatty acyl groups may be represented by formula III
• each R2 is independently selected from an aliphatic chain having at least 4 carbon atoms .
• hort-chain acid may be represented by
• Rx is a Cx ⁇ C4 alkyl.
• Rx may thus be selected from a Cx alkyl, a C2 alkyl, a C3 alkyl or a C4 alkyl .
• the fatty acid(s) and/or the fatty acyl group (s) of the mixed anhydride and of the optional fatty acid anhydride may, in principle, be any fatty acid(s) , including any aliphatic monocarboxylic acid, for example those derived from or contained in esterified form in an animal or vegetable fat, oil or wax .
• the fatty acid(s) and/or the fatty acyl group (s) of the mixed anhydride and of the optional fatty acid anhydride may be linear or branched. They may be saturated or unsaturated. Branched fatty acid(s) may reduce hydrogen bonding between cellulose and/or hemicellulose strands and may thereby help in obtaining easily plasticized cellulose and/ or hemicellulose .
• a fatty acid may, at least in some embodiments, refer to two or more fatty acids, and/or to a mixture of fatty acids. Therefore any references to "a fatty acid” or “the fatty acid” in this specification may, alternatively or additionally, be understood as references to two or more fatty acids, and/or to a mixture of fatty acids.
• the fatty acid(s) may be derived from e.g. a vegetable oil, animal fat, and/or tall oil. Typically such sources may provide a mixture of fatty acids having various compositions. It may be possible e.g. to distil out fatty acids of certain chain lengths and/or other properties and provide such fatty acids for use in the method.
• the fatty acid(s) and/or the fatty acyl group (s) of the mixed anhydride and of the optional fatty acid anhydride may each have 4 to 28 (i.e. 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28) carbon atoms. In certain embodiments, they may have 6 to 20 carbon atoms, or 6 to 16 carbon atoms, or 8 to 16 carbon atoms. The number of carbon atoms may be understood as including the carbon atom of the carboxyl group of the fatty acid/fatty acyl group.
• each R2 may be independently selected from an aliphatic chain having 4 to 28 i.e. 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28) carbon atoms. In certain embodiments, each R2 may be independently selected from an aliphatic chain having 6 to 20 carbon atoms, or 6 to 16 carbon atoms, or 8 to 16 carbon atoms.
• Reactivity of fatty acids may decrease upon increase in the number of carbon atoms; for example, fatty acids having more than 16 carbon atoms may have a lower reactivity.
• fatty acids having longer chains may allow for producing thermoplastic cellulose and/or hemicellulose polymer materials from the esterified cellulose and/or hemicellulose, even in embodiments in which the degree of substitution (DS) is lower.
• a skilled person may therefore select suitable fatty acid(s) and/or number (s) of carbon atoms such that the reactivity and/or the properties of the end product are desirable.
• the short acid anhydride may, at least in some embodiments, be selected from the group of formic anhydride, acetic anhydride, propionic anhydride, acetic propionic anhydride, and any mixtures and combinations thereof. These short acid anhydrides may have boiling points and/or other properties well suited for removing them at least partially from the initial anhydride mixture.
• cellulose and/or hemicellulose may be understood as referring to cellulose; to hemicellulose; and/or to any mixture or combination thereof.
• it may refer to a mixture or composition comprising cellulose and optionally hemicellulose, such as pulp.
• Such a mixture may comprise predominantly cellulose, but also an amount of hemicellulose .
• pulp may typically contain e . g . about 10 - 25 % (w/w) of hemicellulose ; the remaining pulp may be cel lulose , although the pulp may additionally comprise impurities such as lignin residues ( typically less than 1 % (w/w) ) , extractives , and/or ash .
• the cellulose and/or hemicellulose may be modified prior to the esterification .
• the cellulose and/or hemicellulose that is mixed with the anhydride mixture may already be modified .
• Various modifications may be available to cellulose and/or hemicellulose and may be compatible with the esterification according to one or more embodiments described in this specification .
• the cellulose and/or hemicellulose may be modified so as to contain charged ( anionic, cationic, or both) groups prior to the esterification .
• the cellulose and/or hemicellulose may be dry and powdered cellulose and/or hemicellulose , such as dry and powdered chemical pulp, when mixed with the anhydride mixture .
• the cellulose and/or hemicellulose may be physically activated.
• the cellulose and/or hemicellulose may be mechanically activated and optionally dried prior to mixing with the anhydride mixture.
• the cellulose and/or hemicellulose may, alternatively or additionally, be mechanically disintegrated and dry before it is mixed with the anhydride mixture.
• the mechanical activation may be done e.g. by grinding the cellulose and/or hemicellulose.
• the mechanical activation may comprise mechanically pre-treating the cellulose and/or hemicellulose e.g. by refining, using a hammer mill, and/or pulverizing the cellulose and/or hemicellulose e.g. by friction grinding or using a ball mill. This may increase the surface area of the cellulose and/or hemicellulose and possibly cut a portion of the fibers in the cellulose and/or hemicellulose; however, typically the polymer length is not significantly affected.
• the activation may be done to improve access to hydroxyl groups of the cellulose and/or hemicellulose.
• the cellulose and/or hemicellulose may be prepared earlier and stored and/or obtained separately e.g. by purchasing from a supplier, or it may be mechanically or otherwise activated shortly before the esterification. It may be beneficial to use the mechanically activated cellulose and/or hemicellulose relatively shortly after the mechanical activation to optimize esterification results.
• the dry cellulose and/or hemicellulose may thus be in the form of a high surface area powder.
• the cellulose and/or hemicellulose may, additionally or alternatively, comprise or be Kraft pulp, for example never dried Kraft pulp. However, any chemical pulp, such as soda and/or sulfite pulp, may also be used.
• the cellulose and/or hemicellulose, such as pulp may be obtainable from wood or from non-wood materials.
• the cellulose and/or hemicellulose may be prepared from cellulose raw material of a plant origin. The raw material may be based on any plant material that contains cellulose and/or hemicellulose. The plant material may be, for example, wood.
• Non-wood material may be derived from agricultural residues, grasses or other plant substances such as straw, leaves, bark, seeds, hulls, flowers, vegetables or fruits from cotton, corn, wheat, oat, rye, barley, rice, flax, hemp, manila hemp, sisal hemp, jute, ramie, kenaf, bagasse, bamboo or reed.
• HW hardwood
• SW softwood
• different polysaccharide compositions may exist in the cellulose and/or hemicellulose.
• the cellulose may contain hemicelluloses and lignin in varying amounts, depending on plant source and pulping conditions .
• bleached birch pulp has a high xylose content ( 25% by weight ) and a negligible lignin content .
• Pulps are typically complex mixtures of different polysaccharide structures .
• the cellulose and/or hemicellulose may be formed by isolating cellulose and/or hemicellulose from a raw material that contains cellulose by chemical , mechanical , thermo-mechanical , or chemi-thermo- mechanical pulping processes , for example kraft pulping, sulfate pulping, soda pulping, organosolv pulping, and by conventional bleaching processes .
• the cellulose and/or hemicellulose may, in some embodiments , not contain substantial amounts of lignin, or it may contain only traces of lignin or non-detectable amounts of lignin . Thus al so the cellulose and/or hemicellulose may be essentially lignin-free .
• additional solvent may be understood as a solvent added to the esterification mixture in order for the esterification reaction to proceed, apart from the short-chain acid (which may, at least in some embodiments , be considered to be a solvent and/or function as a solvent in the esterification) .
• the acid catalyst is not particularly limited . It may comprise or be a strong acid, such as sulfuric acid and/or hydrochloric acid . However, other acids and acid catalysts may also be contemplated .
• the anhydride mixture may be obtained, the cellulose and/or hemicellulose and the anhydride mixture may be mixed, and the cellulose and/or hemicellulose may be esterified in a single reactor . This may simpl ify the process and/or allow for easier scalability .
• the anhydride mixture and the cellulose and/or hemicellulose may be mixed and the anhydride mixture may esterify the cellulose and/or hemicellulose under mixing, for example under mechanical stirring or kneading .
• the mixing may result in a higher degree of substitution .
• the cellulose and/or hemicellulose may be optionally mechanically activated, the cellulose and/or hemicellulose and the anhydride mixture may be mixed, and the cellulose and/or hemicellulose may be esteri fied in a high consistency processing reactor .
• the mixing and kneading action that may be provided by the high consistency processing reactor may result in a higher degree of substitution of the esterified cellulose and/or hemicellulose ; it may thereby generate less waste than certain other approaches .
• the reagents may be circulated and reused .
• the esterified cellulose and/or hemicellulose obtained may be filtered and/or washed.
• the esterified cellulose and/or hemicellulose obtained may be dried, for example in an oven.
• the esterified cellulose and/or hemicellulose may then be used for various purposes, for example in the preparation of a thermoplastic cellulose and/or hemicellulose polymer material.
• An esterified cellulose and/or hemicellulose is also disclosed.
• the degree of substitution (DS) of fatty acyls in the esterified cellulose and/or hemicellulose may be greater than the DS of short-chain acyls in the esterified cellulose and/or hemicellulose.
• the total DS in the esterified cellulose and/or hemicellulose may be in the range of 0.2 to 3.0, wherein the DS of fatty acyls in the esterified cellulose and/or hemicellulose may be greater than the DS of short-chain acyls in the esterified cellulose and/or hemicellulose.
• the degree of substitution of fatty acyls in the esterified cellulose and/or hemicellulose may be, for example, at least 0.2, or in the range of 0.2 to 3.
• the degree of substitution of short-chain acyls in the esterified cellulose and/or hemicellulose may be up to 2.8, or in the range of 0.2 to 2.8) .
• the degree of substitution may be determined e.g. by nuclear magnetic resonance (NMR) methods .
• thermoplastic cellulose and/or hemicellulose polymer material may further comprise various additives, such as e.g. a filler (for example, inorganic fine particles and/or organic compounds) , a plasticizer, a flame retardant, an antioxidant, a colouring (for example, a colouring pigment) , a masterbatch, etc.
• a filler for example, inorganic fine particles and/or organic compounds
• a plasticizer for example, a plasticizer
• a flame retardant for example, an antioxidant
• a colouring for example, a colouring pigment
• the esterified cellulose and/or hemicellulose and/or the thermoplastic cellulose and/or hemicellulose polymer material may be extruded e.g. into grains, pellets, filaments, or a film or heat pressed to a film. Such films may be slightly transparent or transparent .
• An article obtainable from the esterified cellulose and/or hemicellulose according to one or more embodiments disclosed in this specification or from the thermoplastic cellulose and/or hemicellulose polymer material according to one or more embodiments disclosed in this specification is also disclosed.
• the article may be e.g. extruded, molded or heat pressed.
• the article may be e.g. a container, a casing, a packaging article, a film, a filmic label, a medical device (such as a nozzle) , a plastic or composite profile, or a 3D printing filament.
• a container e.g. a container, a casing, a packaging article, a film, a filmic label, a medical device (such as a nozzle) , a plastic or composite profile, or a 3D printing filament.
• FIG 1 schematically illustrates an embodiment of the esterification process.
• acetic anhydride as the short-chain acid anhydride a mixed anhydride having a fatty acyl group derived from the fatty acid and a short-chain acyl group (acetyl) derived from the short-chain acid anhydride.
• the resulting reactive fatty acid i.e.
• the pulp used in the examples contained, in addition to cellulose, about 25 % (w/w) of hemicellulose; less than 1 % (w/w) of lignin residues; 0.2 % (w/w) extractives; and 0.4 % (w/w) ash.
• the reactor temperature was lowered to at least 60 °C by using water cooling and then 1 1 of 50 % ethanol mixture was carefully poured into the reactor. This extraction took 30 min, and then the suspension was carefully poured into a 10 1 bucket or similar.
• the product was filtered from the dilute acetic acid mixture, mixed with 4 1 of deionized water, washed with water, the procedure being repeated until washings with water gave neutral pH suspension. Water was removed as far as possible by filtration and then the product was dried in an oven at 105 °C.
• Esterified cellulose was produced as described in Example 2, except a 6 h reaction was performed with a Juccheim reactor.
• This reactive fatty acid mixture was added to a batch reactor together with 0.5 g of sulfuric acid catalyst with mixing set to about 11 Hz and the temperature was raised to 80 °C.
• the reactor temperature was lowered to at least 60 °C by using water cooling, and then 1 1 of 50 % ethanol mixture was carefully poured into the reactor. This extraction took 30 min, and then the suspension was carefully poured into a 10 1 bucket or similar.
• the product was filtered from the dilute acetic acid mixture, mixed with 4 1 of deionized water, washed with ethanol and water, the procedure being repeated until washings with water gave neutral pH suspension . Water was removed as far as possible by filtration and then the product was dried in an oven at 105 ° C .
• This mixture was added to a reactor together with 1 mL of sulfuric acid catalyst with mixing set to about 40 rpm, and the temperature was raised to 80 ° C .

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• 2020
  • 2020-11-11 FI FI20206137A patent/FI20206137A1/fi unknown
• 2021
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