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WO2025118173A1 - Marqueurs pour matières plastiques recyclées - Google Patents

Marqueurs pour matières plastiques recyclées Download PDF

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Publication number
WO2025118173A1
WO2025118173A1 PCT/CN2023/136652 CN2023136652W WO2025118173A1 WO 2025118173 A1 WO2025118173 A1 WO 2025118173A1 CN 2023136652 W CN2023136652 W CN 2023136652W WO 2025118173 A1 WO2025118173 A1 WO 2025118173A1
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WO
WIPO (PCT)
Prior art keywords
polymer
moieties
marker
compounds
moiety
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/CN2023/136652
Other languages
English (en)
Inventor
Yaokun HAN
Bing Liang
Zhouhua JI
Yong Zhao
Jie JI
Brian Jazdzewski
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to PCT/CN2023/136652 priority Critical patent/WO2025118173A1/fr
Priority to TW113144559A priority patent/TW202540317A/zh
Publication of WO2025118173A1 publication Critical patent/WO2025118173A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
    • G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
    • G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds

Definitions

  • This invention relates to the field of plastics recycling.
  • BBS 4-bis (2-benzoxazolyl) stilbene
  • Methods are needed to confirm the presence of recycled plastic in a pellet or fabricated article that use only low levels of a marker compound and in which the marker compound is safe for skin contact, is detectable at low concentrations, and is stable in the plastic through multiple fabrication and recycling operations which may subject to marker compound to high heat and shear.
  • One aspect of this invention is a polymer formulation that contains:
  • thermoplastic polymer selected from the group consisting of poly (ethylene terephthalate) (PET) , polyethylene (PE) , polypropylene (PP) and blends that contain at least 50 weight percent PET, PE and/or PP; and
  • thermoplastic polymer (iii) is chemically and thermally stable in contact with the thermoplastic polymer at 280°C for 30 minutes;
  • a second aspect of this invention is process to identifiably indicate the origin or other information about a thermoplastic polymer, comprising the step of homogeneously blending with the thermoplastic polymer at least 0.01 parts per million by weight (ppmw) of one or more marker compounds that each:
  • thermoplastic polymer (c) is chemically and thermally stable in contact with the thermoplastic polymer at 280°C for 30 minutes;
  • marker compounds exclude 4, 4-Bis (2-benzoxazolyl) stilbene (BBS) and the selection and proportions of the marker compounds indicate the origin or other information about the thermoplastic polymer.
  • BSS 4-Bis (2-benzoxazolyl) stilbene
  • a third aspect of this invention is a process to determine the origin of a thermoplastic polymer in a polymer composition comprising the step of analyzing a sample of the polymer composition using a chromatography technique for one or more marker compounds that each:
  • thermoplastic polymer (c) is chemically and thermally stable in contact with the thermoplastic polymer at 280°C for 30 minutes;
  • Suitable chromatographic techniques include gas chromatography-mass spectroscopy (GC/MSD) or high performance liquid chromatography (HPLC) .
  • a fourth aspect of the invention is a process to detect and quantify marker compounds in a polymer composition of this invention comprising the steps of:
  • the marker compounds used in this invention are stable, blend well with thermoplastic polymers, and are readily detected at part-per-billion concentrations by chromatography techniques such as gas-chromatography/mess spectroscopy analysis or high-performance liquid chromatography. When properly selected, the marker compounds can be odorless, they can be approved for skin or food contact, and they can have no noticeable impact on the color or other performance characteristics of the thermoplastic polymer. A wide variety of different specific compounds fall within the class of marker compounds used in this invention, and they can be selected and/or combined to indicate different sources for different polymer streams.
  • thermoplastic polymers This invention is used to provide identification for thermoplastic polymers. It can be used with any thermoplastic polymer. Examples include:
  • PET polyethylene terephthalate
  • PE polyethylene
  • HDPE high density polyethylene
  • LDPE low density polyethylene
  • LLDPE linear low density polyethylene
  • the thermoplastic polymer is selected from the group consisting of PET, PE and PP. In some embodiments, the thermoplastic polymer is a blend that contains at least 50 weight percent PET, PE and/or PP, or at least 60 weight percent or at least 70 weight percent or at least 80 weight percent or at least 90 weight percent or at least 95 weight percent. In some embodiments, the thermoplastic polymer contains up to 100 weight percent PET, PE and/or PP.
  • the thermoplastic polymer contains PET. In some embodiments, the thermoplastic polymer contains at least 50 weight percent PET, or at least 60 weight percent or at least 70 weight percent or at least 80 weight percent or at least 90 weight percent or at least 95 weight percent.
  • the thermoplastic polymer contains PE. In some embodiments, the thermoplastic polymer contains at least 50 weight percent PE, or at least 60 weight percent or at least 70 weight percent or at least 80 weight percent or at least 90 weight percent or at least 95 weight percent.
  • the thermoplastic polymer contains PP. In some embodiments, the thermoplastic polymer contains at least 50 weight percent PP, or at least 60 weight percent or at least 70 weight percent or at least 80 weight percent or at least 90 weight percent or at least 95 weight percent.
  • Suitable polymers are commercially available, and processes to make them are well known.
  • the thermoplastic polymer is a recycled polymer.
  • the recycled polymer resin is pre-consumer/post-industrial recycled polymer.
  • pre-consumer and post-industrial refer to polymers recovered from pre-consumer material, as defined by ISO-14021, such as scraps and waste from polymer manufacturing facilities or from polymer fabricators.
  • pre-consumer polymer thus includes blends of thermoplastic polymers recovered from materials diverted to the waste stream during a manufacturing process.
  • the recycled polymer is post-consumer recycled (PCR) polymer.
  • PCR post-consumer recycled
  • the term “post-consumer recycled” (or “PCR” ) polymer resin refers to polymer resins and blends that were previously used in a consumer application such as packaging or clothing and were recycled after their use was completed. PCR polymer is typically collected from recycling programs and recycling plants. Sources of PCR polymer can include, for example, food and beverage packaging, other product packaging, plastic cutlery, caps and closures, wrappers, clothing, and almost any other item made from thermoplastic polymers.
  • Recycled polymers often differ from “virgin” polymers.
  • First, recycled polymers may have higher levels of impurities than virgin polymers; recycled polymers are likely to pick up contaminants in their previous use, such as stray bits of other polymers or refuse.
  • Second, recycled polymer may have a broader range of molecular weights and other molecular characteristics than virgin polymer, because the recycled polymer is a blend of different polymers that have been recycled.
  • virgin polymer typically contains only the additives needed for its intended purpose, whereas recycled polymer contains any additives that are in the polymers being recycled.
  • Last, recycled polymer has typically been fabricated (for example, molded or extruded) one or more times; this added heat history may cause recycled polymer to have higher levels of carbon, ash and other degraded polymer than virgin polymer.
  • Recycled polymers are commercially available, and processes to make them are well known. Polymers that have been collected and sorted are typically recycled in a multistep process of:
  • steps (a) , (b) and (c) may be altered. See, for example, Grigone, “Methods of Recycling, Properties and Applications of Recycled Thermoplastic Polymers” , 2 Recycling 24 (2017) ; “Mechanical Recycling” published by European Bioplastics e. V. (2020) and “The Complete Plastics Recycling Process” published by Recycle Track Systems at https: //www. rts. com/blog/the-complete-plastics-recycling-process-rts/ .
  • thermoplastic polymer (c) are chemically and thermally stable in contact with the thermoplastic polymer up to at least 280°C for at least 30 minutes;
  • the marker compound contains at least three fused aromatic rings, such as anthracene, phenanthrene, chrysene, pyrene, corannulene, coronene, hexahelicene and ovalene and related compounds having pendant alkyl or alkyl ether moieties.
  • a marker compound that contains three fused ring systems is not anthracene.
  • the fused ring marker compounds contain at least 14 carbon atoms per molecule or at least 15 carbon atoms or at least 16 carbon atoms or at least 17 carbon atoms or at least 18 carbon atoms.
  • the fused ring marker compounds contain at most 40 carbon atoms or at most 32 carbon atoms or at most 24 carbon atoms or at most 20 carbon atoms or at most 18 carbon atoms.
  • the marker compound contains a first aryl moiety with at least two fused aromatic rings linked directly or indirectly to a second aryl moiety through an unfused linkage.
  • marker compounds include phenyl naphthalene, benzyl naphthalene, phenyl anthracene, benzyl anthracene and related compounds having pendant alkyl or alkyl ether moieties.
  • the marker compound contains at least three aryl moieties that are linked directly or indirectly to each other but not fused to each other.
  • the marker compound may meet Formula 1:
  • ⁇ L is an alkyl moiety or an aryl moiety
  • Each of Ar 1 , Ar 2 and Ar 3 is independently an aryl moiety, which may optionally have pendant alkyl or alkoxy moieties;
  • ⁇ R 1 is an alkyl moiety
  • ⁇ a is a number of aryl moieties (Ar 1 ) linked directly to L;
  • ⁇ b is a number of aryl moieties (Ar 2 ) linked to L by ether linkages;
  • ⁇ c is a number of aryl moieties (Ar 3 ) linked to L by alkyl linkages (R 1 ) ;
  • any of a, b and/or c may be “0” , indicating that the relevant moiety is not present in the molecule, but L, a, b, and c are selected so that each molecule contains at least 3 aryl moieties that are not fused with each other.
  • the aryl moieties (Ar 1 , Ar 2 , Ar 3 and optionally L) comprise a single 6 membered ring. In some embodiments, the aryl moieties (Ar 1 , Ar 2 , Ar 3 and optionally L) independently comprise two or more fused rings.
  • the aryl moieties are carbocyclic. In some embodiments, the aryl moieties are heterocyclic, and in some embodiments the heterocyclic rings contain nitrogen, such as pyridinyl or pyrimidinyl moieties. In some embodiments, aryl moieties that contain two fused rings are carbocyclic.
  • each aryl moiety independently contains no more than 18 carbon atoms or no more than 16 carbon atoms or no more than 16 carbon atoms or no more than 12 carbon atoms or no more than 10 carbon or no more than 6 carbon atoms, excluding pendant moieties. In some embodiments, each aryl moiety independently contains at least 4 carbon atoms or at least 5 carbon atoms or at least 6 carbon atoms, excluding pendant moieties. In some embodiments, each aryl moiety is a phenyl ring, which may optionally have pendant moieties.
  • each aryl moiety may independently be unsubstituted, having no pendant moieties other than hydrogen atoms.
  • L is a phenyl ring without pendant moieties other than the pendant moieties illustrated in Formula 1.
  • each aryl moiety may independently have one or more pendant alkyl or alkaryl moieties (-R 2 ) , alkyl ether moieties (-OR 3 ) , or alkaryl ether moieties (-OR 4 Ar 4 ) .
  • alkyl moieties in the marker compound independently contain no more than 18 carbon atoms or no more than 12 carbon atoms or no more than 10 carbon atoms or no more than 8 carbon atoms or no more than 6 carbon atoms.
  • alkyl moieties in L and R 1 independently contain no more than 4 carbon atoms or no more than 3 carbon atoms or no more than 2 carbon atoms. All alkyl moieties contain at least 1 carbon atom.
  • alkyl moieties in R 2 , R 3 and R 4 independently contain at least 2 carbon atoms or at least 3 carbon atoms or at least 4 carbon atoms or at least 5 carbon atoms or at least 6 carbon atoms.
  • the alkyl moieties are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl moieties.
  • alkyl moieties in in L and R 1 are independently methyl or ethyl moieties.
  • R 2 is an alkaryl moiety comprising an alkyl moiety having from 1 to 6 carbon atoms linked to from 1 to 3 aryl moieties.
  • R 2 is a triphenylmethyl moiety.
  • Aryl moieties (Ar 4 ) in alkaryl ether moieties have the same description as given previously for aromatic moieties.
  • the alkaryl ether moieties (-OR 4 Ar 4 ) comprise from 7 to 12 carbon atoms.
  • the marker compounds are selected to be chemically and thermally stable in contact with the thermoplastic polymer at 280°C for 30 minutes, as described below.
  • the marker compounds contain essentially no hydroxyl moieties, acid moieties, aldehyde moieties, ester moieties, amine moieties, amide moieties, nitro moieties or nitrile moieties or halogen atoms; these moieties might potentially form sites for chemical reaction or degradation.
  • the sum of a + b + c is at least 2. In some embodiments, the sum of a + b + c is at least 3. In some embodiments, the sum of a + b + c is at most 6 or at most 5 or at most 4 or at most 3.
  • L is a methyl group
  • the sum of a + b + c is 2 to 4.
  • the sum of a + b + c is 2 or 3, and all moieties shown in Formula 1 are bonded to the same carbon atom.
  • the sum of a + b + c is 2 or 3, and all moieties shown in Formula 1 are bonded to the same ⁇ -carbon atom.
  • at least some moieties shown in Formula 1 are bonded to different carbon atoms.
  • Examples of potential marker compounds are shown in Formulae 4a-4h and homologous compounds or related compounds having one or more pendant alkyl moieties.
  • Each marker compound is selected to have a boiling point of at least 250°C.
  • the marker compound has a boiling point of at least 260°C or at least 275°C or at least 300°C or at least 400°C or at least 500°C. There is no maximum desirable boiling point, but in some embodiment a boiling point above 800°C is unnecessary.
  • the marker compound is selected to be chemically and thermally stable in contact with the thermoplastic polymer at 280°C for 30 minutes, which means that when tested as described in the Test Methods at least 50 percent of the marker remains detectable in the polymer (the percentage of the marker that remains detectable after the test is the “percent stability” ) . In some embodiments, the marker compound has at least 55 percent stability or at least 60 percent or at least 65 percent or at least 70 percent. In some embodiments, the marker compound has 100 percent stability (no measurable loss of the marker compound) . In many embodiments, the marker compounds are subjected to conditions less severe than the Test Methods (lower temperature and/or lower time at maximum temperature) during the blending and processing of the polymer formulation.
  • marker compounds are commercially available.
  • Other marker compounds can be made by known processes. For example,
  • one or more marker compounds are mixed homogeneously with polymer in a concentration of at least 0.01 parts-per-million by weight (ppmw) .
  • the marker compounds and their proportions are selected to identify the source or other information about the polymer. Many different identity codes can be assigned when more than one marker compound is present.
  • One, two, three or more marker compounds may be used to form the code.
  • the marker compounds indicate that the polymer is a recycled polymer.
  • the polymer formulation is intended for end-use fabrication to make useful articles such as fibers, films or shaped articles; it is called an end-use formulation.
  • the end-use formulation contains at least 0.01 ppmw of marker compound or at least 0.02 ppmw or at least 0.05 ppmw.
  • end-use formulation contains at most 2000 ppmw of marker compound or at most 1000 ppmw or at most 750 ppmw or at most 500 ppmw or at most 300 ppmw or at most 200 ppmw or at most 100 ppmw or at most 50 ppmw or at most 20 ppmw.
  • the end-use formulation contains a high enough concentration of marker compounds that the marker compounds can be quantitatively detected when the end-use formulation is blended to make a polymer composition in a 1: 1 weight ratio with other polymers, or a 1: 2 weight ratio or a 1: 5 weight ratio or a 1: 10 weight ratio or a 1: 20 weight ratio.
  • the polymer formulation is intended as a masterbatch; the masterbatch contains a higher concentration of marker compounds and is blended with other polymers to add the marker compounds in a concentration suitable for end use formulations.
  • a masterbatch contains at least 20 ppmw of marker compound or at least 200 ppmw or at least 1000 ppmw or at least 2000 ppmw.
  • a masterbatch contains at most 500,000 ppmw of marker compound (50 weight percent) or at most 200,000 ppmw or at most 100,000 ppmw.
  • the marker compounds produce no detectable odor in the end-use formulation.
  • the marker compounds produce no change in color that is detectable by the naked eye in the end-use formulation.
  • the marker compounds produce no change in transparency that is detectable by the naked eye in the end-use formulation.
  • the marker compounds are non-fluorescent, meaning that under UV light that is safe for human exposure they produce no fluorescence that is visible to the naked eye, in concentration that applies to the end-use formulation.
  • the marker compounds are safe for skin contact, in the end use formulation.
  • the marker compounds are approved for food contact in the end-use formulation.
  • the marker compounds can be blended homogeneously with the polymer by blending in known equipment to soften and mix the polymer, such as mixers, kneaders and extruders. See, for example, White et al., “Polymer Blend Compounding and Processing” , Encyclopedia of Polymer Blends: Volume 2: Processing, First Edition , published by Wiley-VCH Verlag GmbH &Co. (2011) .
  • the blending process takes place at temperature above or equal to the glass-transition temperature of the polymer. In some embodiments, the blending process subjects the polymer to temperatures of at least 170°C or at least 180°C or at least 190°C or at least 200°C.
  • the blending process takes place at a temperature below the boiling point of the marker compounds and below the temperature at which the marker compounds or the polymer suffer significant thermal degradation during the time frame of the process. In some embodiments, the blending process subjects the polymer to temperatures of no more than 300°C or no more than 290°C or no more than 280°C or no more than 270°C or no more than 260°C or no more than 250°C or no more than 230°C or no more than 210°C.
  • other polymer additives may be added to the polymer formulation at the same time as the marker compounds or before or after the marker compounds.
  • examples of other common additives include antistatic agents, color enhancers, dyes, lubricants, fillers, pigments, primary antioxidants, secondary antioxidants, processing aids, UV stabilizers, nucleators, slip agents, antiblock agents, and combinations thereof.
  • other additives make up no more than 60 weight percent of the polymer formulation or no more than 10 weight percent or no more than 5 weight percent or no more than 2 weight percent or no more than 1 weight percent. In some embodiments, other additives make up 0 weight percent of the polymer formulation.
  • the polymer formulations can be used in any application that is known for the base polymer, provide that for use in regulated applications such as food contact or medial applications, the polymer, marker compounds and other additives must meet the regulatory requirements for the application.
  • a PET polymer formulation is spun into clothing fibers.
  • the end-use formulation may be blended with other polymers to form polymer compositions.
  • the presence of the marker compounds and their concentration can identify that the end-use formulation is in the polymer composition, and can show how much end-use formulation is in the polymer composition.
  • the marker compounds can be detected in polymer compositions by known means for detecting trace components in polymer.
  • the marker compounds can be detected and measured in a polymer composition by:
  • GC/MSD gas chromatography-mass spectroscopy
  • HPLC high performance liquid chromatography
  • the marker compounds can be extracted from the ground polymer using a solvent that does not dissolve the polymer.
  • the process of dissolving both the polymer and marker compounds and then precipitating the polymer is quicker and may give more complete recovery.
  • the detection process can detect and quantify the concentration of marker compounds in quantities of no more than 10 parts per million by weight (ppmw) or no more than 5 ppmw or no more than 2 ppmw or no more than 1 ppmw or no more than 0.5 ppmw or no more than 0.2 ppmw or no more than 0.1 ppmw or no more than 50 parts per billion by weight (ppbw) or no more than 10 ppbw.
  • Low detection limits can permit identification of the polymer composition in a mixture with other plastics, even when the polymer composition makes up less than 25 weight percent or 10 weight percent or less of the total mixture of plastics.
  • a 0.1g marked PET sample is dissolved in a sealed glass vial with 1 mL mixed solvent of phenol and carbon tetrachloride (3: 2 wt/wt) that contains 0.4 ⁇ g/mL of p-terphenyl-d14 as an internal standard;
  • THF tetrahydrofuran
  • THF solution is centrifuged to remove the PET deposit. A portion of the supernatant is transferred into a 2 mL GC vial and analyzed using gas chromatography/mass spectrometry detector (GC/MSD) .
  • GC/MSD gas chromatography/mass spectrometry detector
  • LOD limit of detection
  • Recycled PET and the potential marking compounds in Table 1 are obtained.
  • the potential marking compounds are tested for boiling point and thermal stability as described in the Test Methods.
  • Marking compounds M. 1 to M. 4 are examples of the marking compounds used in the invention.
  • C.M. 5 is a comparative example. Tests show that the inventive marker compounds are high boiling and stable at high temperatures, whereas the comparative example is not.
  • a target amount of marker compound shown in Table 2 is added into the amount of r-PET chips shown in Table 2 in a plastic bag, and the marker and chips are shaken together by hand for 1 minute.
  • the mixture is coextruded into a 28mm screw extruder at 260-280°C and pelletized through underwater granulation to produce the marked PET chips.
  • the expected concentration of marker in each formulation (in ppm) is recorded in Table 2.
  • the quantity of marker compounds in each PET formulation is measured using the test shown in the Test Methods, and the measured concentration is recorded in Table 2.
  • Table 2 shows that the inventive marker compounds mix readily with the PET, survive extrusion, and can be reliably detected after extrusion in a quantitative manner.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)

Abstract

Les polymères, et en particulier le PET recyclé, peuvent être marqués pour identifier une origine ou d'autres informations par ajout d'un ou de plusieurs composés marqueurs, chacun: 1. constitué essentiellement de fractions alkyles, de fractions aryles et/ou de fractions éthers ; et 2. contient au moins 3 cycles aromatiques ; et 3. est chimiquement et thermiquement stable en contact avec le polymère thermoplastique à 280 °C pendant 30 minutes ; et 4. a un point d'ébullition d'au moins 250 °C.
PCT/CN2023/136652 2023-12-06 2023-12-06 Marqueurs pour matières plastiques recyclées Pending WO2025118173A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2023/136652 WO2025118173A1 (fr) 2023-12-06 2023-12-06 Marqueurs pour matières plastiques recyclées
TW113144559A TW202540317A (zh) 2023-12-06 2024-11-20 再生塑膠之標記

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Application Number Priority Date Filing Date Title
PCT/CN2023/136652 WO2025118173A1 (fr) 2023-12-06 2023-12-06 Marqueurs pour matières plastiques recyclées

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070071951A1 (en) * 2005-09-29 2007-03-29 James Grande Authenticatable plastic material, articles, and methods for their fabrication
WO2012017987A1 (fr) 2010-08-06 2012-02-09 オートリブ ディベロップメント エービー Rideau gonflable
WO2012177987A1 (fr) * 2011-06-24 2012-12-27 Angus Chemical Company Ethers tritylés
WO2014088898A1 (fr) 2012-12-06 2014-06-12 Angus Chemical Company Éthers de thpe
US9422493B2 (en) 2012-07-06 2016-08-23 Rohm And Haas Company Tritylated alkyl aryl ethers
US20180148564A1 (en) 2016-11-30 2018-05-31 Dow Global Technologies Llc Novel markers for aqueous compositions
US20180148565A1 (en) 2016-11-30 2018-05-31 Rohm And Haas Company Novel markers for aqueous compositions
WO2022214830A1 (fr) * 2021-04-08 2022-10-13 The University Of Manchester Procédé d'analyse de plastique recyclé

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070071951A1 (en) * 2005-09-29 2007-03-29 James Grande Authenticatable plastic material, articles, and methods for their fabrication
WO2012017987A1 (fr) 2010-08-06 2012-02-09 オートリブ ディベロップメント エービー Rideau gonflable
WO2012177987A1 (fr) * 2011-06-24 2012-12-27 Angus Chemical Company Ethers tritylés
US9422493B2 (en) 2012-07-06 2016-08-23 Rohm And Haas Company Tritylated alkyl aryl ethers
WO2014088898A1 (fr) 2012-12-06 2014-06-12 Angus Chemical Company Éthers de thpe
US20180148564A1 (en) 2016-11-30 2018-05-31 Dow Global Technologies Llc Novel markers for aqueous compositions
US20180148565A1 (en) 2016-11-30 2018-05-31 Rohm And Haas Company Novel markers for aqueous compositions
WO2022214830A1 (fr) * 2021-04-08 2022-10-13 The University Of Manchester Procédé d'analyse de plastique recyclé

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
"Mechanical Recycling", 2020, EUROPEAN BIOPLASTICS E.V
ABDOLLAHI ET AL.: "Synthesis of 1, 3, 5-Triarylbenzenes, Using CuCl2 as a New Catalyst", INT'L J MAT & CHEM, vol. 2, no. 4, 2012, pages 128 - 131
GRIGONE: "Recycling", vol. 24, 2017, article "Methods of Recycling, Properties and Applications of Recycled Thermoplastic Polymers"
SCHYNS ET AL.: "Recycled Plastic Content Quantified through Aggregation Induced Emission", ACS SUSTAINABLE CHEM. ENG., vol. 19, 2022, pages 12659 - 69
TIAN-YING HAO: "Authentication of recycled and virgin polyethylene terephthalate based on UPLC-Q-TOF-MS using non-volatile organic compounds and chemometrics", FOOD ADDITIVES & CONTAMINANTS: PART A, vol. 40, no. 8, 3 August 2023 (2023-08-03), pages 1114 - 1130, XP093155058, ISSN: 1944-0049, DOI: 10.1080/19440049.2023.2227732 *
WHITE ET AL.: "Encyclopedia of Polymer Blends", vol. 2, 2011, WILEY-VCH VERLAG GMBH & CO., article "Polymer Blend Compounding and Processing"

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