WO2025078555A1 - Délaminage et/ou désencrage de films plastiques à l'aide de solvants eutectiques profonds - Google Patents

Délaminage et/ou désencrage de films plastiques à l'aide de solvants eutectiques profonds Download PDF

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Publication number
WO2025078555A1
WO2025078555A1 PCT/EP2024/078617 EP2024078617W WO2025078555A1 WO 2025078555 A1 WO2025078555 A1 WO 2025078555A1 EP 2024078617 W EP2024078617 W EP 2024078617W WO 2025078555 A1 WO2025078555 A1 WO 2025078555A1
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plastic material
plastic
organic solvent
deep eutectic
mixture
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English (en)
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Steven DE MEESTER
Sibel ÜGDÜLER
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Universiteit Gent
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Universiteit Gent
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • B29B2017/0203—Separating plastics from plastics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • B29B2017/0213—Specific separating techniques
    • B29B2017/0293—Dissolving the materials in gases or liquids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2009/00—Layered products
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to plastic recycling.
  • a method to deink and/or to delaminate a plastic material, in particular plastic films, is provided.
  • the invention also provides a composition and a kit of parts for deinking and/or delaminating a plastic material, and uses thereof.
  • plastic packaging for instance from post-consumer waste, is currently recovered through open-loop mechanical recycling processes.
  • contamination from both the production and use phase impedes re-use of these recycled plastics in high-value applications.
  • the presence of ink adversely affects the optical and physicochemical properties of recycled plastic films.
  • a mix of inks results in dark-colored pellets after extrusion, thus making the recovered plastic films suitable only for 'downcycled' products.
  • a plastic packaging generally consists of a combination of different types of polymers, each with their own specific functionality in order to obtain superior preservation performances tailored to their specific purpose. Differences in the processing properties of the different polymer layers impedes recycling of multilayer plastic films as they cause incompatibility issues during mechanical recycling. Therefore, delamination and/or deinking methods should be further developed to ensure the recycling of plastic films.
  • EP2832459 Bl describes a deinking technology for monolayer plastic films, which removes inks from different type of plastics through a water-based system.
  • printed plastic films pass through several treatments, including e.g. grinding, deinking, washing, drying, and pelletizing in order to obtain ink-free plastic films.
  • ionic or non-ionic surfactants can be used to remove water-based inks from plastic films.
  • non-ionic surfactants were used together with organic solvents in order to obtain high deinking efficiencies.
  • physico- mechanical properties of recycled film decreases substantially compared to virgin material.
  • volume ratio of the organic solvent and the deep eutectic solvent in the mixture is from 10:90 to 75:25, preferably from 15:85 to 70:30, more preferably from 20:80 to 60:40.
  • the deep eutectic solvent comprises a hydrogen bond acceptor (HBA) selected from the group comprising or consisting of choline chloride, tetrabutyl ammonium bromide, tetramethyl ammonium bromide, acetylcholine, cetyltrimethylammonium bromide and tetra N-butylammonium chloride, preferably choline chloride, and/or, preferably and, a hydrogen bond donor (HBD) which is a carboxylic acid such as a carboxylic acid selected from the group comprising or consisting of oxalic acid, benzoic acid, tartaric acid, adipic acid, lactic acid and citric acid.
  • HBA hydrogen bond acceptor
  • the deep eutectic solvent comprises a HBD and HBA at a molar ratio of between 1:10 and 10:1, preferably between 1:5 and 5:1, more preferably between 1:2 to 2:1, even more preferably about 1:1.
  • the deep eutectic solvent comprises a HBA such as choline chloride and a HBD which is a carboxylic acid such as a carboxylic acid selected from the group consisting of oxalic acid, lactic acid and tartaric acid at a molar ratio of between 1:10 and 10:1, preferably between 1:5 and 5:1, more preferably between 1:2 to 2:1, even more preferably about 1:1.
  • HBA such as choline chloride
  • HBD which is a carboxylic acid such as a carboxylic acid selected from the group consisting of oxalic acid, lactic acid and tartaric acid at a molar ratio of between 1:10 and 10:1, preferably between 1:5 and 5:1, more preferably between 1:2 to 2:1, even more preferably about 1:1.
  • the plastic material comprises one or more polymers selected from the group comprising a polyolefin (such as polyethylene (PE), including low-density polyethylene (LDPE) and high-density polyethylene (HDPE), and polypropylene (PP)), polyethylene terephthalate (PET), polyurethane (PU), polyamide (PA), polystyrene (PS), polycarbonate (PC), ethyl vinyl alcohol (EVOH), ethylene vinyl acetate (EVA), polyvinyl chloride (PVC), and copolymers thereof.
  • PE polyethylene
  • LDPE low-density polyethylene
  • HDPE high-density polyethylene
  • PP polypropylene
  • PET polyethylene terephthalate
  • PU polyurethane
  • PA polyamide
  • PS polystyrene
  • PC polycarbonate
  • EVOH ethyl vinyl alcohol
  • EVA ethylene vinyl acetate
  • PVC polyvinyl chloride
  • plastic material comprises or is provided with an ink such as one type of ink or a plurality of different types of ink.
  • a deinked and/or delaminated plastic material obtainable by the method according to any one of 1 to 26, or a polymer fraction thereof.
  • a kit of parts comprising: a deep eutectic solvent; and an organic solvent having a polarity index of less than 5.5.
  • composition according to 28 or the kit of parts according to 29 for deinking a plastic material comprising or provided with an ink.
  • composition according to 28 or the kit of parts according to 29 for delaminating a multilayer plastic material.
  • composition according to 28 or the kit of parts according to 29 for deinking and delaminating a multilayer plastic material, wherein the deinking and the delamination occurs in a single step.
  • Fig. 1 Single-step delamination and deinking of different types of plastic films using a mixture of DES and organic solvent according to an embodiment of the invention.
  • UV_PP UV-crosslinked ink
  • UV-flexo_PP monolayer cyan colored PP film containing an UV-flexo-crosslinked ink and a coating layer
  • PET/AI/PE multilayer black PET/AI/PE film
  • Fig. 2 Delamination and deinking of different monolayer and multilayer plastic films in mixtures of DES consisting of choline chloride and oxalic acid in 1:1 molar ratio and 10 v%, 25 v%, 50 v% or 75 v% butyl acetate at 80°C during lh contact time.
  • compositions of the plastic films from left to right i) monolayer cyan colored white OPP plastic film containing an UV-crosslinked ink and an overprint varnish (OPV) coating layer, ii) monolayer cyan colored transparent OPP plastic film containing an UV-crosslinked ink, iii) monolayer cyan colored PP film containing an UV-flexo- crosslinked ink and a coating layer, iv) multilayer magenta colored PE/OPP plastic film and v) multilayer black colored PET/AI/PE plastic film.
  • OPP overprint varnish
  • compositions of the plastic films from left to right i) monolayer cyan colored white OPP plastic film containing an UV-crosslinked ink and an overprint varnish (OPV) coating layer, ii) monolayer cyan colored transparent OPP plastic film containing an UV-crosslinked ink, iii) monolayer cyan colored PP film containing an UV-flexo-crosslinked ink and a coating layer, iv) multilayer magenta colored PE/OPP plastic film and v) multilayer black colored PET/AI/PE plastic film.
  • OPP overprint varnish
  • a step means one step or more than one step.
  • the endpoints values of the range are included.
  • the recitation of numerical ranges by endpoints includes all integer numbers and, where appropriate, fractions subsumed within that range (e.g. 1 to 5 can include 1, 2, 3, 4 when referring to, for example, a number of elements, and can also include 1.5, 2, 2.75 and 3.80, when referring to, for example, measurements).
  • the recitation of endpoints also includes the end point values themselves (e.g. from 1.0 to 5.0 includes both 1.0 and 5.0). Any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • wt% refers to a weight percentage of a component, a volume percentage of a component, or molar percentage of a component, respectively, based on the total weight, the total volume of material, or total moles, which includes the component.
  • wt% and “weight%” are used as synonyms herein.
  • the present invention relates to a method for deinking and/or delaminating of a plastic material, the method comprising:
  • the plastic material to be used in the method of the present invention can be any plastic material including plastic packaging, plastic bags, plastic labels, etc.
  • the term plastic material also encompasses plastic waste.
  • Plastic waste may comprise post-industrial plastic waste and postconsumer plastic waste.
  • Post-industrial plastic waste includes plastic material that is used or produced in a manufacturing process and comprises for example plastic films such as stretch films.
  • Post-industrial plastic waste usually comprises homogeneous material, composed of a single polymer type or of a limited number of polymer types and is usually clean.
  • Post-consumer plastic waste includes plastic material that has already been used by the end user and comprises for example bottles, trays, plastic packaging and household items.
  • Post-consumer plastic waste usually comprises a mixture of different polymer materials and may be highly contaminated and dirty.
  • Plastic material encompasses for example waste flows comprising polyolefin based material such as PE or PP, either rigid or non-rigid (films), such waste flows are sometimes referred to as DKR 310 (plastic films), DKR 321 (polyolefin plastic bottles), DKR 323 (mixed polyolefin items), DKR 323-2 (flexible polyolefin items), DKR 324 (polypropylene) and DKR 329 (polyethylene).
  • DKR 310 plastic films
  • DKR 321 polyolefin plastic bottles
  • DKR 323 mixed polyolefin items
  • DKR 323-2 flexible polyolefin items
  • DKR 324 polypropylene
  • DKR 329 polyethylene
  • a plastic film is used.
  • a "plastic film” refers to a continuous polymeric material, which is typically non-rigid or flexible, and usually thin.
  • the plastic material, or plastic film may be composed of one type of polymeric material or may be a blend of two or more types of polymers.
  • An important advantage of the method of the invention is that it can be used with different types of plastics, or combinations of plastics.
  • the plastic material, or plastic film comprises one or more polymers selected from the group comprising or consisting of a polyolefin (such as polyethylene (PE), including low-density polyethylene (LDPE) and high-density polyethylene (HDPE), and polypropylene (PP)), polyethylene terephthalate (PET), polyurethane (PU), polyamide (PA), polystyrene (PS), polycarbonate (PC), ethyl vinyl alcohol (EVOH), ethylene vinyl acetate (EVA), polyvinyl chloride (PVC), and copolymers thereof, preferably a polyolefin and/or PET.
  • a polyolefin such as polyethylene (PE), including low-density polyethylene (LDPE) and
  • the plastic material, or plastic film may typically comprise contaminants and/or dirt.
  • Contaminants refer to components of the plastic material that are not part of the polymeric structure. Contaminants include, for example, but without limitation, additives, coatings such as barrier coatings, metal coatings or biocoatings, adhesives (e.g. glue), inks and labels such as plastic labels or paper labels.
  • adhesives e.g. glue
  • inks e.g. glue
  • labels such as plastic labels or paper labels.
  • dirty refers to impurities that adhere to the plastic material, or plastic film, during their life cycle such as dust, soil, grease, organic waste, etc.
  • the plastic material, or plastic film comprises a metal material such as, for example, aluminium.
  • the plastic material, or plastic film comprises or is provided with ink.
  • the ink, coating and/or adhesive layer that may be present in the plastic materials described herein can be composed of various types of polymers such as, without limitation, polyurethane, nitrocellulose, cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate, methyl methacrylate/butyl methacrylate copolymer, polyvinyl butyral, poly(methyl methacrylate), poly(n-butyl methacrylate), hydroxyl containing copolymer of vinyl chloride and acid esters, polyvinyl acetate, acrylic polymers, etc.
  • the plastic material, or plastic film may have a monolayer structure or a multilayer structure.
  • a "multilayer" plastic material or plastic film refers to a material or film comprising at least two plastic layers configured in an alternating arrangement to form a laminate structure.
  • the plastic material, or plastic film is a multilayer plastic material, or a multilayer plastic film, comprising at least two polymer layers, each polymer layer independently comprising one or more polymers selected from the group comprising or consisting of a polyolefin (such as polyethylene (PE), including low-density polyethylene (LDPE) and high-density polyethylene (HDPE), and polypropylene (PP)), polyethylene terephthalate (PET), polyurethane (PU), polyamide (PA), polystyrene (PS), polycarbonate (PC), ethyl vinyl alcohol (EVOH), ethylene vinyl acetate (EVA), polyvinyl chloride (PVC), and copolymers thereof, preferably a polyolefin and/or PET.
  • a polyolefin such as polyethylene (PE), including low-density polyethylene (LDPE) and high-density polyethylene (HDPE), and polypropylene (PP)
  • PET polyethylene terephthalate
  • PU
  • the multiple plastic layers may be adhered to one another by means of an adhesive layer, e.g. a glue.
  • the two or more plastic layers may be the same or distinct from each other.
  • a multilayer plastic material or plastic film may comprise two PE layers, or a PET layer and a PE layer.
  • a multilayer plastic material is used comprising at least two different plastic layers.
  • a multilayer plastic material or plastic film may further comprise a non-plastic layer such as a metal or metallised layer (e.g. an aluminium layer), or a coating layer (e.g. a varnish).
  • a multilayer plastic material or plastic film may comprise a PET layer and a PE layer, and an Al layer between these polymer layers.
  • the plastic material, or plastic film comprises or is provided with ink.
  • Ink may be provided on an outer surface of a plastic material or plastic film, or may be covered by one or more layers.
  • ink may be provided between two plastic layers of a multilayer plastic material, or between a plastic layer and a coating.
  • Ink can also be embedded in a layer, such as a polymer based layer, a varnish, or barrier layer.
  • the ink can be applied on the plastic material by any technique known in the art, for example a printing technique.
  • the main ingredients of inks are pigments, dyes, solvents, binders and additives, for example surfactants and/or solubilizers.
  • Pigments organic or inorganic or dyes give color and opacity to the ink and may influence the fluidity of the ink.
  • Binders usually low-molecular-weight polymeric resins, disperse the pigments and retain them on the plastic surface after printing.
  • the solvent is a liquid, providing fluidity and allowing the transfer of the ink from the printing system to the substrate.
  • Additives in the ink may for example comprise waxes, surfactants, drying agents and antioxidizing agents.
  • An important advantage of the method according to the present invention is that it allows to deink plastic material comprising or provided with different types of inks, for example with solventbased inks, water based inks, offset inks, UV and/or EB curable inks and any combination thereof.
  • the inks can be cross-linked.
  • Non-limiting examples of solvent-based inks include inks comprising nitrocellulose based resins, polyurethane based resins, polyvinylchloride based resins, ethyl cellulose based resins, cellulose acetate propionate based resins, cellulose acetate butyrate based resins, polyvinyl butyral based resins, polyacrylate based resins, polyamide based resins, and combinations thereof.
  • Non-limiting examples of water-based inks include inks comprising acrylate based resins, maleics based resins or combinations thereof.
  • Non-limiting examples of offset inks include modified rosin resins, in particular phenolic modified rosin resins, alkyd based resins and combinations thereof.
  • Non-limiting examples of ultraviolet curable (UV) and/or electron beam (EB) curable inks include acrylate based resins, for example epoxy acrylate based resins.
  • the plastic material may be provided with or comprise one type of ink or a a combination of different types of inks. eutectic solvent
  • a plastic material is contacted with a deep eutectic solvent (DES) and an organic solvent to deink and/or to delaminate the plastic material.
  • DES deep eutectic solvent
  • the inventors have surprisingly found that a DES can be used as a deinking medium for plastic material.
  • the DES can dissolve adhesive layers, e.g. a glue, and coatings or barrier layers, preferably polymer based coatings or barrier layers, without causing any dissolution or degradation of the plastic layers.
  • a “deep eutectic solvent” or “DES” refers to a mixture formed by self-association of a hydrogen bond donor (HBD) and a hydrogen bond acceptor (HBA), resulting in an eutectic mixture.
  • a complexing agent may be added to the DES mixture.
  • An "eutectic composition” or “eutectic mixture” is well known in the art, and refers to a homogenous mixture of substances that melts or solidifies at a single temperature that is lower than the melting point of any of the constituents.
  • DESs have physicochemical properties that are similar to those of traditional ionic compounds, but compared to these ionic liquids, DESs offer several advantages including their biodegradability and low toxicity, and they are cheap.
  • the compounds of many DES are of natural origin or are primary metabolites (e.g. choline derivatives) and as such, DES can be denoted as natural DES (NADES).
  • DES are categorized under 4 groups: type I (composed of quaternary ammonium salt and metal chloride), type II (quaternary ammonium salt and metal chloride hydrate), type III (quaternary ammonium salt and hydrogen bond donor) and type IV (metal chloride hydrate and hydrogen bond donor).
  • a type III DES is used.
  • Quaternary ammonium salts used in type III DES are ionic compounds containing a quaternary ammonium nitrogen, four alkyl or aryl groups connected to the nitrogen and an anionic ion, e.g., chloride or bromide.
  • alkyl refers to normal, secondary, or tertiary, linear, branched or straight hydrocarbon with no site of unsaturation of formula CnHjn+i wherein n is preferably a number ranging from 1 to 12, preferably from 1 to 6.
  • alkyl may refer to Ci. ⁇ alkyl, for instance Ci-ioalkyl, or Ci- 8 alkyl, or Ci.galkyl, or Ci- 4 alkyl.
  • Ci.galkyl includes all linear or branched alkyl groups with between 1 and 6 carbon atoms, and thus includes methyl, ethyl, 1-propyl (n- propyl), 2-propyl (iPr), 1-butyl, 2-methyl-l-propyl (i-Bu), 2-butyl (s-Bu), 2-dimethyl-2-propyl (t-Bu), 1-pentyl (n-pentyl), 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-l-butyl, 2- methyl-l-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-
  • aryl refers to a monocyclic carbocyclic ring system or a bicyclic carbocyclic fused ring system having one or more aromatic rings.
  • Non-limiting examples of aryl include benzyl, azulenyl, indanyl, indenyl, naphthyl, phenyl, tetrahydronaphthyl, and the like.
  • aryl is intended to include both substituted and unsubstituted aryl unless otherwise indicated.
  • suitable quaternary ammonium salts for a DES include choline chloride, tetrabutyl ammonium bromide, tetramethyl ammonium bromide.
  • a DES is used, wherein the HBA is selected from the group comprising or consisting of choline chloride, tetrabutyl ammonium bromide, tetramethyl ammonium bromide, acetylcholine, cetyltrimethylammonium bromide and tetra N-butylammonium chloride, preferably choline chloride.
  • the other constituent of a type III DES is a hydrogen bond donor (HBD) which supplies the hydrogen atom to form a hydrogen bond with the quaternary ammonium salt.
  • the HBD may be an alcohol, an amide, an urea, a carboxylic acid or an amine.
  • Non-limiting examples of a suitable HBD for a type III DES are among others, phenol, 1,4-butanediol, ethylene glycol, acetamide, benzamide, urea, thiourea, butylamine, phenylamine, benzoic acid, tartaric acid, oxalic acid, adipic acid, lactic acid and citric acid.
  • phenol 1,4-butanediol
  • ethylene glycol acetamide
  • benzamide urea
  • thiourea butylamine
  • phenylamine phenylamine
  • benzoic acid tartaric acid, oxalic acid, adipic acid, lactic acid and citric acid.
  • a DES is used, wherein the HBD compound is a carboxylic acid such as a carboxylic acid selected from the group comprising or consisting of oxalic acid, benzoic acid, tartaric acid, adipic acid, lactic acid and citric acid.
  • carboxylic acid such as a carboxylic acid selected from the group comprising or consisting of oxalic acid, benzoic acid, tartaric acid, adipic acid, lactic acid and citric acid.
  • a DES is used wherein the HBA is selected from the group comprising or consisting of choline chloride, tetrabutyl ammonium bromide, tetramethyl ammonium bromide, acetylcholine, cetyltrimethylammonium bromide and tetra N-butylammonium chloride, preferably choline chloride, and wherein the HBD is a carboxylic acid such as a carboxylic acid selected from the group comprising or consisting of oxalic acid, benzoic acid, tartaric acid, adipic acid, lactic acid and citric acid.
  • a DES is used wherein the HBD is a carboxylic acid such as a carboxylic acid selected from the group consisting of oxalic acid, lactic acid and tartaric acid, and wherein the HBA is choline chloride.
  • the HBA and HBD may be mixed in a molar ratio from 1:10 to 10:1, preferably from 1:5 to 5:1, more preferably from 1:2 to 2:1, even more preferably of about 1:1.
  • a DES is used comprising a carboxylic acid, and choline chloride in a molar ratio from 1:10 to 10:1, preferably from 1:5 to 5:1, more preferably from 1:2 to 2:1, even more preferably of about 1:1.
  • a DES is used comprising oxalic acid and choline chloride in a molar ratio of 1:1.
  • suitable DES include choline chloride:benzoic acid (e.g.
  • choline chloride:tartaric acid e.g. in a molar ratio 1:10 - 10:1 , preferably 1:1
  • choline chloride:adipic acid e.g. in a molar ratio 1:10 - 10:1 , preferably 1:1
  • choline chloridedactic acid e.g. in a molar ratio 1:10 - 10:1 , preferably 1:1
  • choline chloride:citric acid e.g. in a molar ratio 1:10 - 10:1 , preferably 1:1
  • the preparation of a DES is well-known to the skilled person and may entail mixing the HBD and HBA at a desired molar ratio, such as at a molar ratio of 1:1, under continuous stirring for at least 30 minutes, preferably for at least 1 hour.
  • the HBD and HBA are mixed at a temperature above 50°C, preferably above 60°C, more preferably above 70°C such as at 80°C.
  • the plastic material is contacted with a DES and an organic solvent.
  • the organic solvent may act as a swelling agent for the plastic material, as such facilitating diffusion of the DES through the swollen polymer layers of a multilayer plastic material so that the DES can reach inner layers of a multilayered structure where it can react with ink and at the same time achieving delamination of the multilayer plastic material. In this way, simultaneous deinking and delamination of the multilayer plastic material is achieved.
  • the organic solvent may reduce the viscosity of the DES and the mixture, thereby improving the diffusion of the DES through the plastic material compared to the use of a DES alone (without an organic solvent), which generally has a high viscosity.
  • organic solvents with a polarity index of about 5.5 or less, preferably of about 5.0 or less, more preferably of about 4.0 or less are used.
  • apolar organic solvents may be advantageous for use with apolar polymeric materials such as, e.g., PP and PE, that are typically present in plastic materials, in particular plastic films, as taught herein, which may result in faster deinking and delamination.
  • polarity index of a solvent refers to a relative measure of the degree of interaction of the solvent with various polar test solutes. Polarity index as used herein is as described in the article, “Classification of the Solvent Properties of Common Liquids” by Snyder, L. J. Chromatography 92: 223 (1974), incorporated herein by reference.
  • Non-limiting examples of suitable organic solvents include heptane (PI: 0.1), cyclohexane (PI: 0.2), toluene (PI: 2.4), methyl-tert-butyl ether (PI: 2.5), o-xylene (PI: 2.5), chlorobenzene ( PI : 2.7), diethyl ether (PI: 2.8), dichloromethane (PI: 3.1), octan-l-ol (PI: 3.4), isopropyl alcohol (PI: 3.9), n-butyl acetate (PI: 4.0), tetrahydrofuran (PI: 4.0), chloroform (PI: 4.1), ethyl acetate (PI: 4.4), ethyl methyl ketone (PI: 4.7), methanol (PI: 5.1), pyridine (PI: 5.3), 2-methoxyethanol (PI: 5.5).
  • heptane PI: 0.1
  • cyclohexane
  • the plastic material is contacted with both a DES and an organic solvent, wherein the volume ratio of the organic solvent and the DES is at least 10:90.
  • volume ratio of organic solvent and DES refers to the ratio of the volume of the organic solvent over the volume of the DES in the mixture. It has been found that more efficient and/or faster deinking and delamination of the plastic material was obtained when the volume ratio of the organic solvent and the deep eutectic solvent is from 10:90 to 75:25, preferably from 15:85 to 70:30, more preferably from 20:80 to 60:40.
  • a DES and an organic solvent can be contacted with the plastic material simultaneously, or the DES and the organic solvent can be provided in a composition, e.g. a composition as described elsewhere herein, and the composition is contacted with the plastic material.
  • the method comprises an additional step of mixing the deep eutectic solvent and the organic solvent to form a composition or mixture prior to the contacting step, wherein the plastic material is contacted with the composition or mixture.
  • compositions or mixture of a DES and an organic solvent suitable for use in the method of the invention comprising or consisting of a DES as described herein and an organic solvent as described herein, wherein the composition or the mixture comprises at least 10 v/v%, preferably between 10 and 75 v/v%, more preferably between 15 and 70 v/v%, even more preferably between 20 and 60 v/v% of the organic solvent, with v/v% based on the volume of the composition.
  • Additional components may also be present in the composition. For example, surfactants may be added to improve the wetting of the plastic material, or flocculants (e.g. polyacrylamide, Triton 100) may be added.
  • the composition of a DES and an organic solvent is a non-eutectic composition.
  • kit of parts comprising: a DES as described herein; and an organic solvent as described herein, preferably an organic solvent having a polarity index of less than 5.5.
  • the plastic material is in mutual contact with the deep eutectic solvent and the organic solvent such as in a mixture (e.g. not floating). Therefore, in the method of the present invention, the plastic material is contacted with a deep eutectic solvent and an organic solvent to form a mixture.
  • the mixture comprises the DES, the organic solvent, and the plastic material. While the contacting proceeds, at least partially deinked and/or delaminated plastic material, as well as ink, glue and/or other components dissolved from the deinked and/or delaminated plastic material will be present in the mixture as well.
  • Said contacting may be carried out e.g. by immersing the plastic material in a deep eutectic solvent and an organic solvent.
  • the plastic material may be introduced in a container and the DES and the organic solvent may be added, or the plastic material may be introduced in a container wherein the DES and the organic solvent were previously introduced.
  • the plastic material, the DES and the organic solvent are contacted in amounts so that the volume of the plastic material over the total volume of the DES and the organic solvent is ranging from at least 0.01 to at most 10.00, more preferably from at least 0.05 to at most 7.00, from at least 0.10 to at most 5.00, or from at least 0.50 to at most 2.50, even more preferably from at least 0.80 to at most 1.20.
  • the contacting step is carried out at a temperature below 100°C.
  • the plastic material is contacted with the deep eutectic solvent and the organic solvent at a temperature below the melting point of the lowest melting polymer in the plastic material, preferably at least 2 °C, more preferably at least 5 °C, even more preferably at least 10 °C, below the melting point of the lowest melting polymer in the plastic material.
  • the plastic material is contacted with the deep eutectic solvent and the organic solvent at a temperature of at least 50°C such as at least 60°C, 70°C, 75°C, 80°C or 85°C.
  • the plastic material is contacted with the deep eutectic solvent and the organic solvent at a temperature between 50°C and 100°C such as between 55°C and 100°C, between 60°C and 100°C, between 65°C and 100°C or between 70°C and 100°C, preferably between 50°C and 90°C such as between 55°C and 90°C, between 60°C and 90°C, between 65°C and 90°C or between 70°C and 90°C.
  • the method further comprises mechanically agitating the mixture while the plastic material is contacted with the DES and the organic solvent.
  • mechanical agitation such as the stirring, is continued as long as the plastic material is contacted with the DES and the organic solvent.
  • Mechanical agitation can be applied by any method known in the art.
  • the mixture may be stirred (e.g. magnetic stirring, stirring in a continuous stirred tank reactor (CSTR) using a rotating agitator), mixed, or (high-intensity) sonication may be applied.
  • the plastic material is contacted with the deep eutectic solvent and the organic solvent under stirring, preferably the plastic material is contacted with the deep eutectic solvent and the organic solvent under stirring at 300 rpm or more, more preferably at 500 rpm or more.
  • the contact time may be determined by the type of ink, e.g. water- and solvent-based inks requiring shorter contact times than UV-based inks.
  • the plastic material is contacted with the DES and the organic solvent for a suitable period of time, for instance for at least 5, 10, 15 or 30 minutes or for at least 1 hour and/or for less than 4 hours, for less than 2 hours or for less than 1.5 hours such as for about 1 hour or less.
  • the method may comprise an additional step of reducing the size of the plastic material before the contacting step. Too small sizes on the other hand may become unpractical.
  • the plastic material may be reduced in size to obtain plastic material having a sieve diameter between 0.01 cm and 20.00 cm, for example between 0.01 cm and 10.00 cm, between 0.10 cm and 10.0 cm or between 0.10 cm and 4.00 cm, preferably between 0.50 cm and 4.00 cm.
  • the term 'sieve diameter' refers to the size of a sieve opening (the width of a square aperture) through which a particle will pass.
  • Techniques for reducing the size of a plastic material are well-known to the skilled person and may include, for example, cutting, shredding, milling and/or grinding.
  • the plastic material in particular plastic waste, may also or further be subjected to one or more other pre-treatment steps before the contacting step.
  • paper or cardboard may be removed from the plastic material, and/or the plastic material may be sorted.
  • Polymer sorting techniques include, for example, wind shifting, density separation and/or near infra-red (NIR) separation, and as known to the skilled person. of plastic material
  • the inventors have found that deinking and/or delamination of the plastic material can occur with no depolymerization, no dissolution and/or no degradation of the plastic material by using methods according to the invention, allowing the recovery of the delaminated and/or deinked plastic material.
  • the present method thus allows to obtain or recover one or more polymer fractions from a plastic material.
  • the present method enables recycling of one or more polymer fractions from plastic waste for further valorization.
  • To recover the delaminated and/or deinked plastic material it has to be separated from the mixture. This can be performed via traditional separation techniques such as filtration, e.g.
  • the method further comprises a step of separating the deinked and/or delaminated plastic material from the mixture.
  • the deinked and/or delaminated plastic material may be separated from the mixture by filtration such as vacuum filtration.
  • the method may further comprise a step of separating the delaminated plastic layers of the plastic material from one another.
  • the skilled person may rely on well-known separation technologies to achieve this, for example, using wind shifting, density separation and/or near infra-red (NIR) separation.
  • NIR near infra-red
  • deinked and delaminated plastic material obtainable by the method according to the invention.
  • a polymer fraction of a deinked and delaminated plastic material obtainable by the method according to the invention.
  • a "deinked" plastic material refers to a plastic materials as defined herein, wherein the amount of ink present on the plastic material following the method of the invention is less than the amount of ink on the plastic material prior to contacting the DES and the organic solvent.
  • the amount of ink remaining on a deinked plastic material may be less than 70%, less than 60%, less than 50%, less than 40%, less than 30%, less than 20%, or less than 10% of the amount of ink present on the plastic material prior to being contacted with the DES and the organic solvent.
  • the ink may also be completely removed from the plastic material, i.e. the plastic material may be fully deinked.
  • the method Before processing of the deinked and delaminated plastic material, or the polymer fraction, they may need to be rinsed e.g. with water in order to remove organic solvent and DES traces from the plastic material.
  • a rinsing step may also remove e.g. dissolved glue and ink.
  • the method further comprises one or more rinsing or washing steps of the deinked and/or delaminated plastic material, or the polymer fraction.
  • the deinked and/or delaminated plastic material, or the polymer fraction thereof may be subjected to a drying step.
  • the method further comprises: separating the deinked and/or delaminated plastic material from the mixture; optionally separating the delaminated plastic layers of the plastic material from one another to obtain two or more polymer fractions; rinsing the separated deinked and/or delaminated plastic material, or one or more polymer fractions thereof; and optionally drying the rinsed deinked and/or delaminated plastic material, or polymer fraction(s).
  • a regranulation and/or agglomeration and/or extrusion step may be performed before (re-)use of the deinked and/or delaminated plastic material, or the polymer fraction(s) thereof.
  • the method may further comprise a step of recovering ink from the mixture.
  • Recovery steps of for example inks or solvents comprise for examples steps using membrane technologies, adsorption technologies and/or distillation.
  • the DES and the organic solvent do not react with each other and form an immiscible mixture, it is possible to recover the solvents with high purity and lower cost compared to other processes wherein the used reagents usually form an azeotropic mixture, thereby lowering the yield and purity of the recovered reagents.
  • the DES and the organic solvent may be separated from the mixture or the remaining mixture (after separating the deinked and delaminated plastic material from the mixture).
  • Said mixture or remaining mixture may further comprise ink, glue and/or other components dissolved from the plastic material.
  • Suitable separation techniques are known to the skilled person and may include, without limitation, centrifugation, filtration techniques (e.g. membrane filtration), precipitation, adsorption, etc.
  • the method further comprises a step of separating the DES and the organic solvent from the mixture or a remaining mixture.
  • the recovered DES and organic solvent can be reused as such e.g. in the method of the invention, or be subjected to a purification step via well-known purification techniques such as distillation.
  • the two solvents can also be separated e.g. through a density separator. After the density separation, each solvent can be recovered with high yield and purity via well-known purification techniques such as distillation, fractionation, azeotropic distillation or extractive distillation.
  • the method may further comprise: separating the DES and the organic solvent from the mixture or a remaining mixture (after separating the deinked and delaminated plastic material from the mixture); separating the DES and the organic solvent, e.g. by density separation; and optionally purifying the DES and/or the organic solvent.
  • the method may further comprise a step of recovering the ink from the mixture.
  • Ink may be recovered using well-known techniques such as membrane technologies, adsorption technologies and/or distillation.
  • the method to deink and/or to delaminate a plastic material according to the present invention may comprise a continuous or discontinuous (batch) process.
  • a continuous process the plastic material, the DES and the organic solvent (or a composition comprising the DES and the organic solvent) or both the plastic material and the DES and the organic solvent (or a composition comprising the DES and the organic solvent) can be continuously introduced.
  • the DES and the organic solvent are reintroduced to contact the plastic material.
  • the DES and the organic solvent are for example reintroduced after being separated from the mixture (or a remaining mixture) to contact the plastic material in the contacting step by means of a looping system.
  • the printed monolayer and multilayer plastic packaging films were supplied by a printing manufacturing company.
  • Choline chloride (ChCI) >99%
  • oxalic acid (98%) lactic acid (>85%), tartaric acid (>99%) were used for the preparation of DES.
  • DES were prepared by mixing a hydrogen bond acceptor (choline chloride) and a hydrogen bond donor (oxalic acid, lactic acid, tartaric acid) at the specified molar ratio at 80°C under rigorous agitation in a flask with a magnetic stirrer until a homogenous mixture was achieved.
  • An organic solvent butyl acetate, cyclohexane, ethyl acetate, methanol was added to the DES at different volume ratios as indicated (between 10 and 75 v/v% of the solvent) and rigorously agitated.
  • a multilayer plastic packaging film comprising a polyethylene terephthalate (PET) layer, a nitrocellulose-based black ink, an urethane-based white ink, a polyurethane-based adhesive, an aluminium layer and a polypropylene (PP) layer, in this sequence, was reduced in size to squares with a side length of 2 cm.
  • PET polyethylene terephthalate
  • a nitrocellulose-based black ink a nitrocellulose-based black ink
  • an urethane-based white ink a polyurethane-based adhesive
  • an aluminium layer a polypropylene (PP) layer
  • a monolayer plastic packaging film comprising a transparent oriented polypropylene (OPP) substrate, a cross-linked acrylate resin, an UV-based white ink layer and a cyan ink on the top layer, was reduced in size to squares with a side length of 1 cm.
  • OPP transparent oriented polypropylene
  • These plastic films were brought into contact with a mixture of DES consisting of choline chloride and lactic acid (1:2 molar ratio) and cyclohexane (50 v/v%) at 70 °C under continuous stirring with an agitator at 400 rpm during 30 minutes.
  • the transparent OPP film was separated from the medium via filtration.
  • a multilayer plastic packaging film comprising a PET layer, a nitrocellulose-based violet ink, an urethane-based white ink, a polyurethane-based adhesive and a polyethylene (PE) layer, in this sequence, was reduced in size to squares with a side length of 4 cm.
  • These plastic films were brought into contact with a mixture of DES consisting of choline chloride and tartaric acid (1:1 molar ratio) and ethyl acetate (10 v/v%) at 65°C under continuous stirring with an agitator at 300 rpm during 1.5 hours.
  • the multilayer plastic film was fully deinked and delaminated to its constituent polymer layers.
  • the transparent delaminated plastic films (PET and PE films) were separated from the medium via filtration.
  • the multilayer plastic film was fully deinked and delaminated to its constituent polymer layers.
  • the transparent delaminated plastic films (OPP and PE films) were separated from the medium via filtration.
  • a monolayer plastic packaging film comprising an OPP layer, a nitrocellulose/polyurethane resin, and a solvent-based black ink layer, respectively, was reduced in size by a shredder with a sieve diameter of 0.01 cm.
  • the obtained particles were brought into contact with a mixture of DES consisting of choline chloride and oxalic acid (1:1 molar ratio) and methanol (50 v/v%) at 60 °C under continuous stirring with an agitator at 500 rpm during 20 minutes.
  • the transparent OPP film was separated from the medium via filtration.
  • plastic films composed of different types of polymeric material(s) and provided with different types of ink were tested: i) a monolayer cyan colored white OPP plastic film containing an UV-crosslinked ink and an overprint varnish (OPV) coating layer, ii) a monolayer cyan colored transparent OPP plastic film containing an UV-crosslinked ink, iii) a monolayer cyan colored PP film containing an UV-flexo-crosslinked ink and a coating layer, iv) a multilayer magenta colored PE/OPP plastic film and v) a multilayer black colored PET/AI/PE plastic film.
  • the plastic films were reduced in size to squares with a side length of 2 cm.
  • plastic films were brought into contact with a mixture of DES consisting of choline chloride and oxalic acid (1:1 molar ratio) and different concentrations butyl acetate (10 v/v%, 25 v/v%, 50 v/v% or 75 v/v%) at 80 °C under continuous stirring with an agitator at 500 rpm for 1 hour.
  • DES consisting of choline chloride and oxalic acid (1:1 molar ratio
  • butyl acetate 10 v/v%, 25 v/v%, 50 v/v% or 75 v/v%
  • Example 7 The plastic films of Example 7 were reduced in size to squares with a side length of 2 cm. These plastic films were brought into contact with a mixture of DES consisting of choline chloride and oxalic acid (1:1 molar ratio) and 50 v% butyl acetate (PI :4), ethyl acetate (PI: 4.4), methanol (PI: 5.1) or water (PI :10.2) at 60 °C under continuous stirring with an agitator at 500 rpm for 1 hour.
  • DES consisting of choline chloride and oxalic acid (1:1 molar ratio) and 50 v% butyl acetate (PI :4), ethyl acetate (PI: 4.4), methanol (PI: 5.1) or water (PI :10.2)

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  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)

Abstract

L'invention concerne un procédé de désencrage et/ou de délaminage d'une matière plastique, de préférence un procédé de désencrage et de délaminage d'une matière plastique en une seule étape. Le procédé comprend la mise en contact de la matière plastique avec un solvant eutectique profond (DES) et un solvant organique à une température inférieure à 100°C pour former un mélange, le rapport de volume du solvant organique et du solvant eutectique profond dans le mélange étant d'au moins 10:90.
PCT/EP2024/078617 2023-10-12 2024-10-11 Délaminage et/ou désencrage de films plastiques à l'aide de solvants eutectiques profonds Pending WO2025078555A1 (fr)

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EP1419829A1 (fr) 2002-11-18 2004-05-19 Duchenaud Uniflexo Procédé de recyclage de support d'impression imprimé de type film plastique et installation pour la mise en oeuvre dudit procédé
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EP2832459B1 (fr) 2012-03-26 2017-04-26 Universidad De Alicante Procédé destiné à éliminer l'encre imprimée sur des films plastiques
WO2020221920A1 (fr) * 2019-05-01 2020-11-05 Novochem Green Additives 4 B.V. Composition de recyclage eutectique
WO2022013482A1 (fr) 2020-07-17 2022-01-20 Lappeenrannan-Lahden Teknillinen Yliopisto Procédé de séparation d'au moins une fraction de polymère à partir d'un matériau comprenant des textiles, ainsi que des fractions de polymère spécifiques et leurs utilisations
CN115433301A (zh) * 2022-10-12 2022-12-06 中国科学院大连化学物理研究所 一种乙烯-乙烯醇共聚物及其制备方法和应用
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EP2832459B1 (fr) 2012-03-26 2017-04-26 Universidad De Alicante Procédé destiné à éliminer l'encre imprimée sur des films plastiques
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