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WO2025247973A1 - Procédé de recyclage d'au moins une polyoléfine contenant des impuretés - Google Patents

Procédé de recyclage d'au moins une polyoléfine contenant des impuretés

Info

Publication number
WO2025247973A1
WO2025247973A1 PCT/EP2025/064792 EP2025064792W WO2025247973A1 WO 2025247973 A1 WO2025247973 A1 WO 2025247973A1 EP 2025064792 W EP2025064792 W EP 2025064792W WO 2025247973 A1 WO2025247973 A1 WO 2025247973A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyolefin
mpa
solvent
particularly preferably
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/064792
Other languages
German (de)
English (en)
Inventor
Johannes Schneider
Andreas MÄURER
Tanja Fell
Renate Leizinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Publication of WO2025247973A1 publication Critical patent/WO2025247973A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
    • C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
    • 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
    • B29B2017/0213—Specific separating techniques
    • B29B2017/0293—Dissolving the materials in gases or liquids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • 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 invention relates to a process for recycling at least one polyolefin containing impurities, in which polymer-containing waste containing the at least one polyolefin is provided and the at least one polyolefin is selectively dissolved in at least one solvent.
  • at least one precipitating agent is added to the polyolefin solution, wherein, before, during, or after this addition, the temperature of the mixture is adjusted to melt a portion of the at least one polyolefin and to form a melt phase and a liquid phase with a higher proportion (relative to the total polyolefin mass in the polyolefin solution) compared to the melt phase, i.e., a higher mass of polyolefin.
  • the melt phase is mechanically separated from the liquid phase, and the liquid phase and/or the melt phase is dried to obtain a low-impact polyolefin fraction and an impurity-enriched polyolefin fraction. Fraction as solids.
  • Plastic waste often contains contaminants that have transferred to the plastic products during manufacturing (e.g., printing inks, processing aids), during use (e.g., contact materials, the environment), or during disposal (e.g., cross-contamination by other waste). Even with solvent-based recycling, these contaminants can often only be insufficiently removed through pretreatment or filtration processes and thus remain in the recycled material. This leads to undesirable discoloration and odors in the material and can also negatively affect its processability and mechanical properties.
  • contaminants e.g., printing inks, processing aids
  • these contaminants can often only be insufficiently removed through pretreatment or filtration processes and thus remain in the recycled material. This leads to undesirable discoloration and odors in the material and can also negatively affect its processability and mechanical properties.
  • solvent-based recycling processes for separating coarser contaminants after solid-liquid separation utilize extraction processes (WO 2022/029318 Al) or liquid filtration processes (WO 2018/068973 Al) with the use of an additional solvent, immiscible with the solvent used, for further purification of dyes, pigments, or degradation products. Nevertheless, fine particles, such as soot, often remain in the recyclate, which cannot be separated by these processes and impair the color of the recyclate, resulting in an undesirable gray tone.
  • Another method for purifying polymer solutions is to precipitate the polymer from the solution by cooling or adding a precipitating agent.
  • the target polymer can be completely precipitated, while the impurities remain in the solvent and are removed together from the polymer by solid-liquid separation (EP 1 888 677 Bl).
  • this method also has limited effectiveness, as fine dirt particles often remain trapped in the precipitating polymer and are therefore not separated.
  • the object of the present invention was to provide a process for recycling polyolefins that enables improved separation of impurities and at the same time allows the process to be carried out as economically and ecologically as possible, e.g. with the lowest possible solvent usage.
  • a process for recycling at least one polyolefin containing impurities comprising the following steps: a) providing polymer-containing waste containing the at least one polyolefin, b) selectively dissolving the at least one polyolefin in at least one solvent, c) adding at least one precipitating agent to the polyolefin solution from step b), wherein, before, during and/or after the addition in step c), a temperature of the mixture is set which leads to the melting of part of the at least one polyolefin and to the formation of a melt phase and a liquid phase, d) mechanically separating the melt phase from the liquid phase, and e) drying the liquid phase and/or the melt phase to obtain a low-impact polyolefin fraction and an impurity-enriched polyolefin fraction as solids.
  • the process according to the invention allows impurities to be removed from a polymer solution by partial precipitation using a precipitating agent.
  • the process is particularly suitable for polymer solutions made of polyethylene and polypropylene. These can, for example, originate from the solvent-based recycling of mixed waste fractions.
  • Suitable solvents and precipitants can be identified using Hansen's solubility parameters.
  • the at least one solvent has a value for the hydrogen bond strength ⁇ H of the Hansen solubility parameter of 0 to 10.0 MPa 0 ⁇ 5, preferably of 0.1 to 6.0 MPa 0 ⁇ 5, particularly preferably of 0.2 to 3.0 MPa 0 ⁇ 5 and / or preferably a value for the polar bond strength ⁇ P of the Hansen solubility parameter of 0 to 8.0 MPa 0 ⁇ 5 , preferably of 0.1 to 5.0 MPa 0 ⁇ 5 , particularly preferably of 0.2 to 3.0 MPa 0 ⁇ 5 .
  • the at least one solvent contains hydrocarbon compounds, preferably aliphatic hydrocarbon compounds, particularly preferably cycloaliphatic linear or branched hydrocarbon compounds, especially cycloaliphatic linear or branched hydrocarbon compounds with 5 to 18 carbon atoms and mixtures thereof, or consists thereof.
  • hydrocarbon compounds preferably aliphatic hydrocarbon compounds, particularly preferably cycloaliphatic linear or branched hydrocarbon compounds, especially cycloaliphatic linear or branched hydrocarbon compounds with 5 to 18 carbon atoms and mixtures thereof, or consists thereof.
  • the at least one precipitating agent has a value for the hydrogen bond strength 6H of the Hansen solubility parameter of at least 5.0 MPa 0-5 , preferably in the range of 8.0 to 15.0 MPa 0-5, particularly preferably from 12.0 to 22.0 MPa 0-5 and / or preferably a value for the polar bond strength 6P of the Hansen solubility parameter of 4.0 to 20.0 MPa 0-5 , preferably from 4.0 to 17.0 MPa 0-5 , particularly preferably from 6.0 to 15.0 MPa 0-5 .
  • the at least one precipitating agent preferably contains an alkyl ester, more preferably a dicarboxylic acid dialkyl ester, particularly preferably a dimethyl ester o- the diethyl ester of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid and mixtures thereof, or consists thereof.
  • the polymer content in the polymer solution can preferably be from 1 to 20 wt.%, preferably from 2 to 15 wt.%, and particularly preferably from 4 to 10 wt.%.
  • the temperature during precipitation in step c) is essentially the same as, or above, the dissolution temperature.
  • the precipitation temperature and the dissolution temperature are in the range of 115 °C to 190 °C, and particularly preferably in the range of 130 °C to 160 °C.
  • the ratio between the amount of solvent and the amount of precipitating agent required to achieve partial precipitation of the polymer depends on the temperature of the solution and is preferably in the range of 3:1 to 1:5, more preferably in the range of 3:1 to 1:4, and particularly preferably in the range of 2.5:1 to 1:3.
  • the mixture of solvent and precipitant has a density greater than that of the melt phase.
  • the mixture of solvent and precipitant has a density ⁇ 1 g/ cm3 , more preferably ⁇ 0.9 g/ cm3 , more preferably ⁇ 0.8 g/ cm3 , and particularly preferably ⁇ 0.75 g/ cm3 .
  • the precipitation process is initiated by adding the precipitating agent at the required process temperature.
  • the precipitating agent can be added at a higher or lower temperature, followed by cooling or heating the mixture to the process temperature. Under these process conditions, a portion of the polymer precipitates as a polymer-rich liquid melt phase, while the remainder stays as a second liquid phase in a polymer-poor precipitating solution. Less than 50% of the polymer precipitates in the liquid melt phase.
  • the fine particulate impurities in the solution i.e., dyes, pigments, and degradation products such as soot and titanium dioxide, are essentially bound in the melt phase, thus purifying the precipitate solution. Due to the concentration of impurities, the melt phase has a dark gray to black color, while the The remaining precipitate solution is whitish to light green in color.
  • the process conditions are chosen so that as little polymer as possible enters the melt phase, but as many impurities as possible are bound in it.
  • the melt phase collects on the surface of the precipitation solution and can be easily separated there using process technology. This can preferably be achieved by filtration or decantation of the precipitation solution. This removes impurities such as dyes, pigments, fine particles, or cross-linked regions in the polymer. Since the described process also results in size separation of the polymer molecules into the two phases, partial precipitation can also be used to adjust the molar mass. Similarly, in conjunction with molar mass fractionation (the high-molecular-weight polymer chains preferentially aggregate in the melt phase), targeted adjustments of the rheological product properties (molecular weight, melt viscosities during processing, and optimized extrusion and processing temperatures) can be achieved. This allows for more uniform and quality-assured product properties, even with highly inhomogeneous waste compositions.
  • step e) is carried out at a temperature preferably of 25 to 275 °C, preferably of 100 to 265 °C, particularly preferably of 150 to 250 °C.
  • a preferred embodiment provides that the drying in step e) is carried out by evaporation of the solvent or precipitation of the polyolefin by adding a precipitating agent or lowering the temperature, followed by mechanical separation and subsequent evaporation of the solvent.
  • the dried product is colorless to slightly greenish.
  • the inventive method offers the advantage that minute impurities, which cannot be separated from the polymer by other processes, collect there by precipitating a sub-fraction and can thus be selectively and effectively removed from polymer solutions.
  • the Precipitation in the form of a melt achieves significantly higher purification performance with less material loss.
  • the form of a cohesive melt phase and its buoyancy due to its lower density allow for much easier separation of the precipitated sub-fraction.
  • a further advantage of the process according to the invention is that precipitation results in a significantly lower proportion of solvent being bound in the polymer fractions. This considerably reduces the energy required for drying these fractions. Additionally, separation by molar mass can be achieved by precipitating a sub-fraction. The precipitated polymer contains significantly longer polymer chains than the remaining solution. Separation of different types of the same plastic from a mixed solution is also possible.
  • HDPE and LDPE types can be fractionated, and polyolefinic homopolymers and copolymers can be separated.
  • the inventive process also enables the separation of different polyolefins, such as the enrichment or fractionation (up to complete recovery as a purified fraction) of a polyolefin (especially PP) from a mixed polyolefin solution containing a mixture of different polyolefins, such as LLDPE, LDPE, HDPE, and PP.
  • purified PP can be recovered from a waste mixture containing both PE and PP.
  • a polyolefin recyclate is also provided, which can be produced according to the previously described process.
  • the polyolefin recyclate contains at least one solvent in the range of a maximum of 1000 ppm and at least one precipitating agent in the range of a maximum of 1000 ppm.
  • the proportion in the polyolefin recyclate of the at least one solvent is in the range of 50 to 500 ppm and/or of the at least one precipitating agent is in the range of 50 to 500 ppm.
  • Fig. 1 shows a photographic image of recycled material samples according to the invention compared to non-inventive samples.
  • FIG 1 shows photographic images of 500 pm thick press films. The following are shown:
  • a waste fraction containing polyethylene (PE), polypropylene (PP), and polyethylene terephthalate (PET) is dissolved in the solvent mixture CreaSolv® PO63 Hl at 115 °C.
  • a dark gray solution (sample 2) is obtained, rich in PE and containing fine particulate impurities in addition to the plastic.
  • CreaSolv® FR1 By adding the precipitating agent CreaSolv® FR1 in a 1:1 ratio to the solvent and increasing the temperature to 148 °C, a small portion of the polymer precipitates from the solution, while the majority remains dissolved.
  • the precipitated polymer appears as a highly viscous, polymer-rich melt, is dark gray-black in color, and collects on the surface of the solution.
  • the solution undergoes a significant lightening to a light green color.
  • the two phases are separated by skimming off the floating melt or by draining the solution.
  • the polymer remaining in the solution (sample 3) is then dried, has a light green color after drying and is largely particle-free (Fig. 1). Drying the polymer in the melt phase (sample 4) additionally yields a black-colored product with a high proportion of fine particles.
  • a color value determination can be performed in the LAB color space. For comparability of different recyclates, the recyclate samples are pressed into round press films with a thickness of 500 ⁇ m using a hydraulic hot press.
  • the LAB color value is determined according to DIN EN ISO/CIE 11664-4 using a DigiEye-700 mm Cube color measurement system from the manufacturer VeriVedi with DigiEye software version 2.8.0.3.
  • the CIEDE2000 color difference can be calculated according to DIN EN ISO/CIE 11664-6. Table 1 shows the LAB color values of the dried samples and their CIEDE2000 color difference to a reference sample of natural (transparent) LDPE virgin material of type Lupolen 1800H (sample 1).
  • Table 1 shows the high purification of the solution through precipitation, resulting in a color difference of 11 between the dried solution with precipitation (sample 3) and virgin material (sample 1). Without precipitation (sample 2), a significantly higher color difference of 33 to virgin material is observed. The accumulation of the removed contaminants in the filtered precipitated polymer (sample 4) is evident from the high color difference of 43 to virgin material (sample 1).
  • a waste fraction containing PE, PP, and PET was dissolved in the solvent mixture CreaSolv® PO63 Hl at 115 °C. After separating the undissolved components, a dark gray PE solution (sample 2) rich in PE and containing fine particulate impurities in addition to the plastic was obtained. Lowering the temperature to 97 °C caused partial precipitation of the solution. The precipitated polymer appeared as dark gray-black flakes in the solution. The two phases were separated by filtration. The polymer remaining in solution (sample 5) was then dried and, after drying, had a dark greenish-gray color (Fig. 1). Drying the filtered-off polymer (sample 6) yielded an additional dark gray product.
  • the ratio of polymer remaining in solution to precipitated polymer was 1:5.
  • a color value determination in the LAB color space and a calculation of the CIEDE2000 color difference between the dried samples 5 and 6 and the new product can be performed.
  • Table 1 shows that only one The low level of purification achieved by precipitation results in a high color difference of 31 between the dried solution with precipitation (sample 5) and the virgin material (sample 1), only slightly below the color difference of 33 of the control sample without precipitation (sample 2).
  • a slight enrichment of the removed contaminants in the filtered precipitated polymer (sample 6) is indicated by the color difference of 38 compared to the virgin material (sample 1).

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Mechanical Engineering (AREA)
  • Sustainable Development (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention concerne un procédé de recyclage d'au moins une polyoléfine contenant des impuretés, consistant à fournir des déchets présentant une teneur en polymères et refermant la ou les polyoléfines et à dissoudre sélectivement cette ou ces polyoléfines dans au moins un solvant. Le procédé consiste ensuite à ajouter un agent de précipitation à la solution de polyoléfine, la température du mélange étant ajustée avant, pendant ou après cette addition, de manière à faire fondre une partie de la ou des polyoléfine et à former une phase fondue et une phase liquide présentant, par rapport à la phase fondue, une proportion plus élevée (par rapport à la masse totale de polyoléfine dans la solution de polyoléfine), c'est-à-dire une masse plus importante de polyoléfine. Le procédé consiste ensuite à effectuer une séparation mécanique de la phase fondue de la phase liquide, puis à sécher la phase liquide et/ou la phase fondue, de manière à obtenir une fraction de polyoléfine appauvrie en impuretés et une fraction de polyoléfine enrichie en impuretés sous forme de matières solides.
PCT/EP2025/064792 2024-05-29 2025-05-28 Procédé de recyclage d'au moins une polyoléfine contenant des impuretés Pending WO2025247973A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102024204994.8A DE102024204994B3 (de) 2024-05-29 2024-05-29 Verfahren zum Recycling mindestens eines Verunreinigungen enthaltenden Polyolefins
DE102024204994.8 2024-05-29

Publications (1)

Publication Number Publication Date
WO2025247973A1 true WO2025247973A1 (fr) 2025-12-04

Family

ID=95981678

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/064792 Pending WO2025247973A1 (fr) 2024-05-29 2025-05-28 Procédé de recyclage d'au moins une polyoléfine contenant des impuretés

Country Status (2)

Country Link
DE (1) DE102024204994B3 (fr)
WO (1) WO2025247973A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018679A1 (fr) 2001-08-21 2003-03-06 Der Grüne Punkt - Duales System Deutschland Ag Procede pour purifier des matieres plastiques
EP1888677B1 (fr) 2005-06-08 2010-08-04 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procede de recyclage de matieres plastiques et application dudit procede
WO2018068973A1 (fr) 2016-10-10 2018-04-19 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procédé de recyclage de déchets contenant des polyoléfines
WO2022029318A1 (fr) 2020-08-07 2022-02-10 Apk Ag Procédé de prétraitement de matière plastique et de recyclage à base de solvant de matière plastique

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19744436A1 (de) 1997-10-08 1999-04-15 Lindner Wolfgang Verfahren zur Gewinnung von polyolefinischen Kunststoffen
US11408098B2 (en) 2019-03-22 2022-08-09 Global Materials Development, LLC Methods for producing polymer fibers and polymer fiber products from multicomponent fibers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003018679A1 (fr) 2001-08-21 2003-03-06 Der Grüne Punkt - Duales System Deutschland Ag Procede pour purifier des matieres plastiques
EP1888677B1 (fr) 2005-06-08 2010-08-04 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procede de recyclage de matieres plastiques et application dudit procede
WO2018068973A1 (fr) 2016-10-10 2018-04-19 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procédé de recyclage de déchets contenant des polyoléfines
WO2022029318A1 (fr) 2020-08-07 2022-02-10 Apk Ag Procédé de prétraitement de matière plastique et de recyclage à base de solvant de matière plastique

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