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WO2025114330A1 - Utilisation d'amines secondaires et/ou tertiaires aliphatiques linéaires ou ramifiées, pour la stabilisation de matières thermoplastiques exemptes d'halogènes, de préférence de matières plastiques recyclées, contre la dégradation oxydative, thermique ou actinique, composition de matière thermoplastique, procédé de stabilisation - Google Patents

Utilisation d'amines secondaires et/ou tertiaires aliphatiques linéaires ou ramifiées, pour la stabilisation de matières thermoplastiques exemptes d'halogènes, de préférence de matières plastiques recyclées, contre la dégradation oxydative, thermique ou actinique, composition de matière thermoplastique, procédé de stabilisation Download PDF

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Publication number
WO2025114330A1
WO2025114330A1 PCT/EP2024/083701 EP2024083701W WO2025114330A1 WO 2025114330 A1 WO2025114330 A1 WO 2025114330A1 EP 2024083701 W EP2024083701 W EP 2024083701W WO 2025114330 A1 WO2025114330 A1 WO 2025114330A1
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WO
WIPO (PCT)
Prior art keywords
styrene
agents
linear
halogen
polyethylene
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/EP2024/083701
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German (de)
English (en)
Inventor
Rudolf Pfaendner
Jannik HALLSTEIN
Elke Metzsch-Zilligen
Kim HAO NG
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
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Publication of WO2025114330A1 publication Critical patent/WO2025114330A1/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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene
    • 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
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/22—Thermoplastic resins

Definitions

  • Plastic recyclates are a growing market and an important element in the circular economy of raw materials. Ideally, recyclates should replace virgin plastics with an identical or at least comparable property profile. However, recyclates from the production of plastic parts (so-called “post-industrial” recyclates) and from collections of used plastics (so-called “post-consumer” recyclates) differ chemically from virgin plastics.
  • post-industrial recyclates e.g., compounding, extrusion, or injection molding
  • applications e.g., high temperatures and/or UV light
  • irreversible changes in the polymer chains occur due to mechanochemical, chemical, or light-induced processes (see, for example, R.
  • the chemical modifications resulting from the damage and aging process primarily involve the formation of hydroperoxide groups, aliphatic carbonyl groups, alcohol groups, acid groups, ester groups, and peracid groups, i.e. structures that are not usually present in virgin polyolefins, for example, and only form as a result of oxidation processes (J. Pospisil et al. Macromol. Symp. 1998, 135, 247-263). Furthermore, recyclates often contain unsaturated structures, i.e. vinylene, vinylidene, and vinyl groups, the former of which can even be conjugated. Unsaturated structures arise through chain scission and disproportionation reactions (H. Hinsken et al., Pol. Degr. Stab.
  • the structural inhomogeneities of a recyclate influence the plastic properties, such as the mechanical properties, processing behavior or morphology. Due to the newly formed chemical structures, recyclates or pre-damaged plastics are more sensitive to oxidation than virgin material, as they act as initiator sites for further oxidation or as prodegradants (A. S. Maxwell, Pol. Eng. Sci. 2008, 381-385, 1. H. Craig, J. R. White, J. Mater.. Sci. 2006, 41, 993-1006, S. Luzuriaga et al. Pol. Degr. Stab. 2006, 91, 1226-1232, C. Signoret et al., Journal of Polymers and the Environment 2020, 28, 2055-2077, F. P.
  • phenolic antioxidants and phosphites such as those described in EP 0662101 (stabilization composition consisting of a phenolic antioxidant, a phosphite, and a fatty acid salt) or EP 0556614 (stabilization composition for mixed plastics consisting of a phenolic antioxidant and a phosphite/phosphonite), are potentially volatile, migrating, and extractable components.
  • stabilizing compositions have been obtained, for example, through inorganic additives, as claimed in US 6525158, US 6251972 (Stabilizing composition consisting of a phenolic antioxidant, a phosphite and a metal oxide such as calcium oxide) or in EP1849822 (Method for suppressing hydrochloric acid in recycling of waste plastics).
  • these inorganic additives are present in the recyclates as particles and can therefore negatively influence the surface properties and complicate production processes through water absorption.
  • stabilizing compositions for recyclates have already been proposed in WO 97/30112 which are phenol- and phosphite-free and do not require inorganic additives.
  • WO 2020/152337 describes stabilizers for recyclates that can react with carbonyl groups, thus leading to improved stabilization of recyclates.
  • Primary amines among others, are used. Secondary and tertiary amines are not mentioned there, as they cannot react with carbonyl groups.
  • the object of the present invention was therefore to propose stabilizers for plastics, especially for recyclates, that are both highly effective and, due to an oligomeric/polymeric structure, exhibit low volatility and are free of aromatic structures.
  • This challenging task was solved by using aliphatic secondary and/or tertiary amine structures, and in particular polyethyleneimines, to stabilize plastics, especially recyclates.
  • the present invention thus relates to the use of linear or branched aliphatic secondary and/or tertiary amines for stabilizing halogen-free thermoplastics, preferably halogen-free thermoplastic recyclates, against oxidative, thermal or actinic degradation.
  • the linear or branched secondary or tertiary amines are liquid or solid and have a boiling point of > 200 °C or have a molecular weight of > 1000 g/mol.
  • the linear or branched aliphatic secondary and/or tertiary amine is selected from the group consisting of polyethyleneimines, alkanolamines and N-methyl-D-glucamine.
  • Suitable alkanolamines are in particular tris(hydroxyalkylamines) and dihydroxyalkylamines with N-substituted long-chain alkyl groups, as well as heterocyclic hydroxyethyl compounds such as triethanolamine, tris(2-hydroxy-1-propyl)amine, n-butyl-N,N-bis(2-hydroxyethyl)amine, N,N-bis(2-hydroxyethyl)_N-oleylamine, N,N-bis(2-hydroxyethyl)-N-palmitylamine, N,N-bis(2-hydroxyethyl)-N-stearylamine, N-(2-hydroxy-3-octyloxypropyl)diethanolamine, N-2-hydroxyethyl)-morpholine.
  • triethanolamine tris(2-hydroxy-1-propyl)amine
  • n-butyl-N,N-bis(2-hydroxyethyl)amine N,N-bis(2-hydroxyethyl)_N
  • Preferred polyethyleneimines are selected from the group consisting of molecules of the following formulas where n and m are each an integer between 3 and 100.
  • Amino acids are also excluded from the invention, since primary amines are generally present in the form of zwitterions, which are accordingly inactive for the present stabilizing effect.
  • a further preferred embodiment provides that the totality of all linear or branched aliphatic secondary and/or tertiary amines is contained in the halogen-free thermoplastic in a weight proportion of 0.01 to 10.00 wt.%, preferably 0.02 to 5.00 wt.%, particularly preferably 0.05 to 3.00 wt.%, in particular 0.10 to 2.00 wt.%.
  • the halogen-free thermoplastic is particularly preferably selected from the group consisting of a) polymers made of olefins or diolefins such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methylpentene-1, polybutadiene, polyisoprene, such as natural rubber (NR), polycyclooctene, polyalkylene-carbon monoxide copolymers, and copolymers in the form of statistical or block structures such as polypropylene-polyethylene (EP), EPM or EPDM with e.g.
  • a) polymers made of olefins or diolefins such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobut
  • EVA ethylene-vinyl acetate
  • ethylene-acrylic esters such as ethylene butyl acrylate, ethylene-acrylic acid and their salts (ionomers), as well as terpolymers such as ethylene-acrylic acid-glycidyl (meth)acrylate
  • graft polymers such as polypropylene-graft-maleic anhydride, polypropylene-graft-acrylic acid, polyethylene-graft-acrylic acid, polyethylene-polybutyl acrylate-graft-maleic anhydride as well as blends such as LDPE/LLDPE or long-chain branched polypropylene copolymers produced with alpha-olefins as comonomers such as 1-butene, 1-hexene, 1-octene or 1-octadecene, b) polystyrene, polymethylstyrene, poly-
  • polystyrene or polyamides e.g., polyphenylene oxides and blends with polystyrene or polyamides, g) polymers of cyclic ethers such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran, h) polyurethanes, made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates such as 2,4- or 2,6 Toluene diisocyanate or methylenediphenyl diisocyanate, in particular linear polyurethanes (TPU), polyureas, i) Polyamides such as polyamide 6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 11, polyamide 12 and (partially) aromatic polyamides such as polyphthalamides, e.g.
  • polyimides Polyimides, polyamideimides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, Polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins, k) polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as polyethylene terephthalate (PET), polybutylene
  • the polymers or polymer blends or recyclates are essentially halogen-free, i.e. free from chlorine- or fluorine-containing polymers such as PVC or PVDC and contain less than 0.5%, preferably less than 0.2%, halogen-containing polymers.
  • a preferred embodiment is the use for stabilizing polyolefins or polystyrenes according to a) and b) of the above list.
  • a particularly preferred embodiment provides for the use of the linear or branched aliphatic secondary and/or tertiary amines for stabilizing polyolefin recyclates, very particularly preferably polyethylene and/or polypropylene recyclates, or relates to the thermoplastic polymer compositions formed therefrom.
  • Polyethylene recyclates are, in particular, HDPE, LDPE, LLDPE, and MDPE.
  • Polypropylene recyclates are, in particular, polypropylene homopolymers and copolymers with polyethylene or mixtures thereof. Post-consumer recyclates are particularly preferred recyclates.
  • At least one further additive is selected from the group consisting of primary antioxidants, secondary antioxidants, UV absorbers, light stabilizers, in particular hindered amines as light (HALS) and long-term heat stabilizers (HAS), metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, transparency improvers (clarifiers), impact modifiers, plasticizers, lubricants, rheology or viscosity modifiers, thixotropic agents, chain extenders, processing aids, mold release agents, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, hydrophobizing agents, surface modifiers, hydrolysis stabilizers, adhesion promoters, dispersants, comp- patibilizers, oxygen scavengers, acid scavengers, acetaldehyde and
  • the at least one additive is selected from the group consisting of phenolic antioxidants, phosphites, phosphonites, sulfites, polyols, acid scavengers, hindered amines and mixtures and combinations thereof.
  • the at least one additive is further preferably present in an amount of 0.01 to 50 wt.%, preferably from 0.01 to 9.99 wt.%, more preferably from 0.01 to 4.98 wt.%, particularly preferably from 0.02 to 2.00 wt.%, based on the totality of all linear or branched aliphatic secondary and/or tertiary amines, the halogen-free thermoplastic and the at least one additive, or is added in a corresponding amount.
  • the present invention also relates to a thermoplastic composition containing or consisting of at least one halogen-free thermoplastic, in particular a halogen-free thermoplastic recyclate and at least one linear or branched aliphatic secondary or tertiary amine, in particular at least one polyethyleneimine.
  • thermoplastic composition contains
  • 0.01 to 10.00 wt.% preferably from 0.02 to 5.00 wt.%, particularly preferably from 0.05 to 3.00 wt.%, in particular 0.10 to 2.00 wt.% of at least one linear or branched aliphatic or tertiary amine,
  • 0.01 to 50.00 wt.% preferably from 0.01 to 9.99 wt.%, more preferably from 0.01 to 4.98 wt.%, particularly preferably from 0.02 to 2.00 wt.% of at least one additive contains or consists of.
  • At least one primary and/or secondary antioxidant is included as at least one additive, preferably in a weight amount of 0.01 to 3.00 wt.%, particularly preferably 0.05 - 2.0 wt.%.
  • the present invention relates to a process for stabilizing halogen-free thermoplastics, in particular plastic recyclates, against oxidative, thermal or actinic degradation by adding at least one linear or branched aliphatic secondary and/or tertiary amine, in particular at least one polyethyleneimine, to the plastic.
  • the present invention relates to a molded part which contains or consists of a thermoplastic composition as described above.
  • the molded part is selected from the group consisting of
  • Packaging e.g. for food, detergents, cosmetics, adhesives in the form of films, bottles, bags, screw-top jars
  • Construction applications such as profiles, construction foils, cable ducts, house cladding, noise barriers, drainage channels, professional boards, floor coverings
  • a post-consumer polypropylene recyclate from battery boxes (manufacturer: BSB Braubach) was homogenized in a polymer powder/additive mixture with the stabilizers according to the invention and extruded in a twin-screw microextruder (MC15HT, manufacturer: Xplore Instruments BV) at 210 °C and a speed of 200 rpm for 30 minutes in a circular motion.
  • the torque retention was measured.
  • the torque curve is a measure of the formulation's stability during processing; the higher the torque retention over time, the better the processing stabilization.
  • PEI-2 Polyethylenimine (branched), Supplier: ThermoScientific Molecular weight: 10,000 g/mol
  • AO-1 Pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate)
  • P-l Tris-(di-tert. butyl phenyl) phosphite
  • a post-consumer polypropylene recyclate from battery boxes (manufacturer: BSB Braubach) in a polymer powder/additive mixture with the stabilizers according to the invention and extruded in a twin-screw microextruder (MC15HT, manufacturer: Xplore Instruments BV) at 210 °C and a speed of 200 rpm for 30 minutes in a circular motion, and the torque retention was measured.
  • the torque curve is a measure of the formulation's stability during processing; the higher the torque retention over time, the better the processing stabilization.
  • PEI-1 Polyethylenimine (branched), Supplier: ThermoScientific Molecular weight: 25,000 g/mol
  • PEI-2 Polyethylenimine (branched), Supplier: ThermoScientific Molecular weight: 10,000 g/mol
  • PEI-3 Polyethylenimine (branched), Supplier: ThermoScientific Molecular weight: 1,200 g/mol
  • PEI-4 Polyethylenimine (linear), Supplier: ThermoScientific Molecular weight: 10,000 g/mol
  • ERY Erythritol
  • AO-1 Pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate)
  • a post-consumer polyethylene recyclate from injection molding waste (manufacturer: Kunststoff Recycling Grünstadt GmbH) was homogenized in a polymer powder/additive mixture with the stabilizers according to the invention. Processing was carried out in a twin-screw extruder (HAAKE PolyLab OS, manufacturer: ThermoScientific, 16 mm, L/D 25) at a temperature profile ranging from 180 °C (feed) to 255 °C (die), a speed of 200 rpm, and a target throughput of 2.0 kg/h. The resulting granules were then processed four more times at a target throughput of 2.0 kg/h.
  • the melt volume flow rate is a measure of the stability of the formulation during processing; the more constant and higher the melt volume flow rate is across multiple extrusions, the better the processing stabilization.
  • PEI-1 Polyethylenimine (branched), Supplier: ThermoScientific Molecular weight: 25,000 g/mol
  • ERY Erythritol CS: Calcium stearate, Supplier: Baerlocher
  • AO-1 Pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate)

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne l'utilisation d'amines secondaires et/ou tertiaires aliphatiques linéaires ou ramifiées pour stabiliser des matières thermoplastiques, de préférence des matières plastiques recyclées, contre la dégradation oxydative, thermique ou actinique.
PCT/EP2024/083701 2023-11-29 2024-11-27 Utilisation d'amines secondaires et/ou tertiaires aliphatiques linéaires ou ramifiées, pour la stabilisation de matières thermoplastiques exemptes d'halogènes, de préférence de matières plastiques recyclées, contre la dégradation oxydative, thermique ou actinique, composition de matière thermoplastique, procédé de stabilisation Pending WO2025114330A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102023211970.6A DE102023211970A1 (de) 2023-11-29 2023-11-29 Verwendung von linear oder verzweigt aliphatischen sekundären und/oder tertiären Aminen, zur Stabilisierung von thermoplastischen Kunststoffen vorzugsweise Kunststoff-Rezyklaten gegen oxidativen, thermischen oder aktinischen Abbau, thermoplastische Kunststoffzusammensetzung, Verfahren zur Stabilisierung sowie Formteil
DE102023211970.6 2023-11-29

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WO2025114330A1 true WO2025114330A1 (fr) 2025-06-05

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Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288748A (en) * 1963-06-27 1966-11-29 Universal Oil Prod Co Stabilization of olefin polymers with nu-hydrocarbyl-alkanolamines
US3389119A (en) * 1965-03-15 1968-06-18 Du Pont Polyethylene compositions stabilized with a tertiary amine and a phenol
US3551381A (en) * 1968-01-17 1970-12-29 Fmc Corp Saturated linear polyesters thermally stabilized with amines
US4172192A (en) * 1977-04-04 1979-10-23 Kemerica, Inc. Process for stabilizing thermoplastic polyurethanes and stabilized product
EP0556614A1 (fr) 1992-02-03 1993-08-25 Rutgers, The State University Procédé et appareil pour l'analyse isotopique
EP0662101A1 (fr) 1992-09-25 1995-07-12 Ciba SC Holding AG Procede de stabilisation et melanges stabilisants pour les melanges plastiques recycles
WO1997030112A1 (fr) 1996-02-15 1997-08-21 Ciba Specialty Chemicals Holding Inc. Stabilisation de produits de recyclage de polyolefines
US6251972B1 (en) 1992-09-25 2001-06-26 Ciba Specialty Chemicals Corp. Process for the stabilization of and stabilizer mixtures for single-material recycled plastics
US6525158B1 (en) 1992-09-25 2003-02-25 Ciba Specialty Chemicals Corporation Process for the stabilization of a stabilizer mixtures for recycled plastic mixtures
US20030195296A1 (en) * 2000-06-29 2003-10-16 Burkhardt Dames Stabilized thermoplastic moulding materials
EP1849822A1 (fr) 2005-02-14 2007-10-31 Kabushiki Kaisha Meiji Gomu Kasei Méthode d'inhibition de l'apparition d'acide chlorhydrique au cours du recyclage de rebuts de matières plastiques
US8173728B2 (en) * 2006-02-01 2012-05-08 Basf Se Stabilizer composition for polymers
US8268920B2 (en) * 2008-12-16 2012-09-18 Basf Se Heat aging resistant polyamides
US20200032034A1 (en) * 2018-07-27 2020-01-30 Milliken & Company Polymeric amine antioxidants
WO2020152337A1 (fr) 2019-01-24 2020-07-30 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procédé permettant de stabiliser des produits de recyclage en matière synthétique, thermoplastiques, exempts d'halogènes, composition en matière synthétique, composition stabilisatrice et utilisation de la composition stabilisatrice
WO2022264524A1 (fr) * 2021-06-15 2022-12-22 国立大学法人東北大学 Inhibiteur d'oxydation, agent améliorant l'activité d'inhibition de l'oxydation, procédé d'inhibition d'oxydation et procédé pour améliorer l'activité d'inhibition de l'oxydation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL285535A (fr) 1961-11-17
GB1570178A (en) 1976-10-15 1980-06-25 Durham Chem Compositions for stabilisation of vinyl chloride polymers
MXPA03005290A (es) 2000-12-13 2003-10-06 Crompton Vinyl Additives Gmbh Sistema de estabilizadores destinados a la estabilizacion de polimeros con un contenido de halogeno.
DE102021205168A1 (de) 2021-05-20 2022-11-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Verwendung mindestens einer Schwefel enthaltenden Aminosäure zur Stabilisierung von thermoplastischen Kunststoff-Recyclaten, stabilisiertes thermo-plastisches Kunststoffrecyclat, Stabilisatorzusammensetzung, Masterbatch sowie Formmasse bzw. Formteil

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288748A (en) * 1963-06-27 1966-11-29 Universal Oil Prod Co Stabilization of olefin polymers with nu-hydrocarbyl-alkanolamines
US3389119A (en) * 1965-03-15 1968-06-18 Du Pont Polyethylene compositions stabilized with a tertiary amine and a phenol
US3551381A (en) * 1968-01-17 1970-12-29 Fmc Corp Saturated linear polyesters thermally stabilized with amines
US4172192A (en) * 1977-04-04 1979-10-23 Kemerica, Inc. Process for stabilizing thermoplastic polyurethanes and stabilized product
EP0556614A1 (fr) 1992-02-03 1993-08-25 Rutgers, The State University Procédé et appareil pour l'analyse isotopique
US6525158B1 (en) 1992-09-25 2003-02-25 Ciba Specialty Chemicals Corporation Process for the stabilization of a stabilizer mixtures for recycled plastic mixtures
US6251972B1 (en) 1992-09-25 2001-06-26 Ciba Specialty Chemicals Corp. Process for the stabilization of and stabilizer mixtures for single-material recycled plastics
EP0662101A1 (fr) 1992-09-25 1995-07-12 Ciba SC Holding AG Procede de stabilisation et melanges stabilisants pour les melanges plastiques recycles
WO1997030112A1 (fr) 1996-02-15 1997-08-21 Ciba Specialty Chemicals Holding Inc. Stabilisation de produits de recyclage de polyolefines
US20030195296A1 (en) * 2000-06-29 2003-10-16 Burkhardt Dames Stabilized thermoplastic moulding materials
EP1849822A1 (fr) 2005-02-14 2007-10-31 Kabushiki Kaisha Meiji Gomu Kasei Méthode d'inhibition de l'apparition d'acide chlorhydrique au cours du recyclage de rebuts de matières plastiques
US8173728B2 (en) * 2006-02-01 2012-05-08 Basf Se Stabilizer composition for polymers
US8268920B2 (en) * 2008-12-16 2012-09-18 Basf Se Heat aging resistant polyamides
US20200032034A1 (en) * 2018-07-27 2020-01-30 Milliken & Company Polymeric amine antioxidants
WO2020152337A1 (fr) 2019-01-24 2020-07-30 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Procédé permettant de stabiliser des produits de recyclage en matière synthétique, thermoplastiques, exempts d'halogènes, composition en matière synthétique, composition stabilisatrice et utilisation de la composition stabilisatrice
WO2022264524A1 (fr) * 2021-06-15 2022-12-22 国立大学法人東北大学 Inhibiteur d'oxydation, agent améliorant l'activité d'inhibition de l'oxydation, procédé d'inhibition d'oxydation et procédé pour améliorer l'activité d'inhibition de l'oxydation

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
A. S. MAXWELL, POL. ENG. SCI., 2008, pages 381 - 385
C. SIGNORET ET AL., JOURNAL OF POLYMERS AND THE ENVIRONMENT, vol. 28, 2020, pages 2055 - 2077
F. P. LA MANTIA ET AL., POLYMERS, vol. 15, 2023, pages 2173
H. HINSKEN ET AL., POL. DEGR. STAB., vol. 34, 1991, pages 279 - 293
I. H. CRAIGJ. R. WHITE, J. MATER.. SCI., vol. 41, 2006, pages 993 - 1006
J. POSPISIL ET AL., MACROMOL. SYMP., vol. 135, 1998, pages 247 - 263
J. POSPISIL ET AL., POL. DEGR. STAB., vol. 48, 1995, pages 351 - 358
M. S. RABELLOJ. R. WHITE, POLYM. DEGR. STAB., vol. 56, 1997, pages 55
R. JIN ET AL., CHEMOSPHERE, vol. 317, 2023, pages 137913
R. PFAENDNER ET AL., ANGEW. MAKROMOL. CHEMIE, vol. 232, 1995, pages 193 - 227
R. PFAENDNER, POLYMER DEGRADATION AND STABILITY, vol. 203, 2022, pages 110082
S. LUZURIAGA ET AL., POL. DEGR. STAB., vol. 91, 2006, pages 1226 - 1232
X. TAO ET AL., J. POLYM. ENVIRON., vol. 28, 2020, pages 2616 - 2630

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