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WO2025022386A1 - Vitrimères, leurs procédés de production et leurs utilisations pour la compatibilisation de mélanges de polymères - Google Patents

Vitrimères, leurs procédés de production et leurs utilisations pour la compatibilisation de mélanges de polymères Download PDF

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Publication number
WO2025022386A1
WO2025022386A1 PCT/IL2024/050721 IL2024050721W WO2025022386A1 WO 2025022386 A1 WO2025022386 A1 WO 2025022386A1 IL 2024050721 W IL2024050721 W IL 2024050721W WO 2025022386 A1 WO2025022386 A1 WO 2025022386A1
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WIPO (PCT)
Prior art keywords
vitrimer
polyolefin
containing molecule
anhydride
presently disclosed
Prior art date
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Pending
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PCT/IL2024/050721
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English (en)
Inventor
Naum NAVEH
Shmuel Kenig
Hanna Dodiuk-Kenig
Natanel JARACH
Karin ROSENFELD
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Shenkar College of Engineering and Design
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Shenkar College of Engineering and Design
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Publication of WO2025022386A1 publication Critical patent/WO2025022386A1/fr
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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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/092—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2310/00—Masterbatches

Definitions

  • Z. Bauer describes synthesis of vitrimer blends with polybutadiene as the majority component, poly(vinylmethylsiloxane-co-dimethylsiloxane) as the minority component, and benzene diboronic ester dithiol as the crosslinker.
  • a vitrimer comprising at least two polyolefin backbones, at least one of the at least two polyolefin backbones being connected, at least once, with one other of said at least two polyolefin backbone of the at least two polyolefin backbones, said connection being via a diester containing bridge having a general formula (I)
  • X represents a valence bond or a chemical moiety
  • L and L' are independently a valence bond or a chemical linker to said polyolefin backbone; and wherein said at least two polyolefin backbones may be the same or different within said vitrimer.
  • MB masterbatch
  • Also provided by a third aspect of the presently disclosed subject matter is a method for obtaining a vitrimer, the method comprises reacting in a reaction mixture an epoxy containing molecule with an anhydride containing molecule, at least one of said epoxy containing molecule and said anhydride containing molecule is grafted on a polyolefin backbone, said reaction forms a diester containing bridge between one polyolefin backbone and one other polyolefin backbone in said reaction mixture.
  • a method of polymer compatibilization comprising: providing a polymeric mixture comprising at least two incompatible synthetic polymers and a compatibilization agent, and; subjecting said polymeric mixture to mixing under shear forces; wherein said compatibilization agent comprises at least one of
  • the presently disclosed subject matter provides, in accordance with a sixth of its aspects, articles of manufacture comprising the presently disclosed vitrimers or the presently disclosed homogenous blends comprising the presently disclosed vitrimer.
  • Figure 1 is a diagram describing a mechanism of preparing P-Hydroxy Ester (BHE) composition in accordance with some examples of the present disclosure.
  • Figure 2 is a plot describing a Fourier Transform Infra-Red (FTIR) spectrum of a P-Hydroxy Ester (BHE) composition according to some examples of the present disclosure.
  • FTIR Fourier Transform Infra-Red
  • Figures 3A-3D are graphs of Differential Scanning Calorimetry (DSC) analyses, where Figure 3A is a DSC graph of a neat BHE sample in accordance with the present disclosure; Figure 3B is a DSC graph of BHE-Moprylene (5:95 wt:wt) mixture in accordance with the present disclosure; Figure 3C is a DSC graph of BHE-SW75 (5:95 wt:wt) mixture in accordance with the present disclosure; and Figure 3D is a DSC graph of SW-Bigbagim-BHE mixture (47.5:47.5:5 wt:wt:wt) in accordance with the present disclosure.
  • DSC Differential Scanning Calorimetry
  • the process of compatibilization involves adding compatibilizers, which are molecules that can bond to two or more types of plastics and promote their mixing.
  • compatibilizers are molecules that can bond to two or more types of plastics and promote their mixing.
  • the plastic types that are incompatible can be made to blend more homogeneously, which can increase the strength and durability of the final composite material.
  • Vitrimers are group of reversible covalently crosslinked polymers. While in crosslinked state, vitrimers are stable and possess improved mechanical properties similarly to thermosetting polymers. When the crosslinked state is unlocked by an external stimulus (e.g., heating, light, and pH), vitrimers demonstrate true thermoplastic behavior.
  • an external stimulus e.g., heating, light, and pH
  • the present disclosure is based on the development of a vitrimer for use, inter alia, in compatibilization of polymers.
  • vitrimer is used herein to denote a polymer material that has the ability to undergo reversible breaking and reformation of covalent bonds when subjected to a suitable stimulus, such as heat, light, physical trigger (e.g. shear forces), chemical trigger and others.
  • the presently disclosed subject matter provides a vitrimer comprising at least two polyolefin backbones, at least one of the at least two polyolefin backbones being connected, at least once, with one other polyolefin backbone of the at least two polyolefin backbones, said connection being via a diester containing bridge.
  • polyolefin as used herein, should be understood to have its commonly known meaning, including, a polymer that are derived from polymerization of olefin monomers, such as ethylene, propylene, butene, and hexene and others.
  • olefin monomers such as ethylene, propylene, butene, and hexene and others.
  • polyolefin encompasses a homopolymer and a copolymer.
  • polyolefin backbone is to be understood to encompass the polyolefin carbohydrate backbone, however, which can be substituted by heteroatom containing moieties, aromatic moieties and the like, while still maintaining the vitrimer's functionality of being able to undergo the reversible breaking and reformation of covalent bonds.
  • the at least two polyolefin backbones can represent the same or different polyolefins. In some examples of the present disclosure the least two polyolefin backbones comprise at least two different polyolefins.
  • polystyrene resin As appreciated by those versed in the art of polymer chemistry two different polyolefin molecules can differ from each other based on several factors, including their molecular weight, number of repeating monomer units, tacticity, degree of branching, the presence of comonomers and other factors and combinations of such factors.
  • the at least two polyolefin backbones polyolefins differ in at least one of their monomeric unit.
  • the at least two polyolefin backbones differ in their molecular weight.
  • the at least two polyolefin backbones differ in number of monomeric units.
  • the at least two polyolefin backbones differ in their tacticity.
  • the different polyolefins may, independently, be isotactic, syndiotactic, and atactic.
  • the at least two polyolefin backbones comprise at least one monomeric unit selected from the group consisting of methylene, ethylene, propylene, pentene, octene, butane and any combinations of same, such as ethyl ene-octene, propylene butane.
  • the at least two polyolefin backbones are selected from the group consisting of polyethylene, polypropylene, polymethylpentene, ethylene-octene copolymer, and propyl ene-butane copolymer.
  • the at least two polyolefin backbones are linked one to the other through a diester containing bridge.
  • L and L' are be same or different within a single vitrimer.
  • At least one of L and L' comprises any one of an aliphatic chain, an aliphatic ring, an aromatic ring, and any combinations of same, the chain or ring optionally including a heteroatom.
  • L or L' comprise independently an acrylate moiety (i.e. an acrylate moiety which may be the same or different within the diester bridge). In some examples of presently disclosed subject matter, L or L' comprise independently an acrylate moiety selected from the group consisting of alkyl acrylate, alkyl methacrylate, acrylic acid and methacrylic acid.
  • L and L' are both methacrylate.
  • X is a phenyl ring and L and L' are both methacrylate.
  • the chemical bridge has the formula (II):
  • the vitrimer according to the presently disclosed subject matter forms a crosslinked three-dimensional network structure.
  • Cross-linking involves the formation of covalent bonds between polyolefin chains, which results in the formation of a network comprising a plurality of polyolefin backbones being cross-linked one to another through a plurality of said diester containing bridges.
  • the vitrimer according to the presently disclosed subject matter, can be characterized by a degree of crosslinking.
  • degree of crosslinking is used to denote the extent to which a polymer network comprising the presently disclosed vitrimer is interconnected through covalent ester bonds between individual polyolefin backbones.
  • the degree of crosslinking is a measure of the density of these ester bonds, and can be expressed in terms of the number or weight of crosslinks per unit volume or mass of the polymer network.
  • the degree of crosslinking is represented as the fraction of monomers in the polymer that have been crosslinked and expressed in mole%. In some examples of the presently disclosed subject matter, the degree of crosslinking of the vitrimer is within a range of about 0.1 mole% and about 10 mole%.
  • the degree of crosslinking of the presently disclosed vitrimers can be measured by any one of Differential Scanning Calorimetry (DSC), Dynamic Mechanical Analysis (DMA) or Nuclear Magnetic Resonance (NMR).
  • DSC Differential Scanning Calorimetry
  • DMA Dynamic Mechanical Analysis
  • NMR Nuclear Magnetic Resonance
  • the degree of crosslinking is indirectly evaluated by analyzing the dynamic viscosity of the crosslinked network of polymers. Without being bound by theory, when the degree of crosslinking increases, the viscosity of the vitrimer also increases, reflecting the increased density of the covalent bonds in the polymer network.
  • dynamic viscosity or “absolute viscosity” is used to denote measure of material's resistance to flow under an applied force or stress. It is defined as the ratio of the shear stress to the shear rate in a material, expressed in units of Pascal-seconds (Pa s) or centipoise (cP).
  • the dynamic viscosity of the presently disclosed vitrimers are within a range of about 10 2 to 10 6 Pa s when measured at 1 Hz/sec' 1 and about 10 1 to 10 4 Pa s when measured at 100 Hz/sec' 1 , at times between about 500 to 7000 Pa s when measured at 10 Hz/sec' 1 .
  • the vitrimer(s) can be a priori formed into a masterbatch. It has been found that it is possible to homogeneously blend the presently disclosed vitrimers with a variety of synthetic polymeric carriers to be used as masterbatch (MB) formulations.
  • MB masterbatch
  • such masterbatch formulation can be formed into pellets, as further described hereinbelow.
  • the presently disclosed subject matter provides, in accordance with a second aspect thereof, a MB comprising the presently disclosed vitrimer(s) blended with one or more synthetic polymeric carriers.
  • the polymeric carrier is characterized by a first viscosity and a vitrimer is characterized by a second viscosity.
  • the first viscosity i.e. that of the polymeric carrier, is lower than the second viscosity, i.e. of the vitrimer.
  • the polymeric carrier within the MB comprises one or more polyolefins.
  • the one or more polyolefins in the MB is selected from the group consisting of polyethylene (PE), polypropylene (PP), polyvinyl, polyvinyl alcohol, polyvinyl pyridine, polyolefin styrene and combinations of same.
  • the polymeric carrier comprises a polyolefin that is identical to at least one of the at least two polyolefin backbones of the presently disclosed vitrimer.
  • the polymeric carrier comprises a combination of polymers, at least one being other than a polyolefin, such as polyester, polyamide, EVOH and polyurethane.
  • the amount of the vitrimer in the MB can vary depending on the specific need of the MB.
  • the amount of the vitrimer can be defined by the weight ratio between the polymeric carrier and the vitrimer.
  • the weight ratio between the polymeric carrier and the vitrimer ranges from about 99: 1 to about 50:50; at times from about 99: 1 to about 97:3; at times from about 98:2 to about 96:4; at times from about 95:5 to about 93:7; at times from about 92:8 to about 90: 10; at times from about 89: 11 to about 87: 13; at times from about 86: 14 to about 84:16; at times from about 83: 17 to about 81 : 19; at times from about 80:20 to about 78:22; at times from about 77:23 to about 75:25; at times from about 74:26 to about 72:28; at times from about 71 :29 to about 69:31; at times from about 68:32 to about 66:34; at times from about 65:35 to about 63:37; at times from about 62:38 to about 60:40; at times from about 59:41 to about 57:43
  • the vitrimer and for the same reason, the MB may comprise trace amounts of a catalyst.
  • the presence of trace amounts of a catalyst is due to the involvement of a catalyst in the process of obtaining the presently disclosed vitrimer.
  • the epoxy containing molecule is selected from the group comprising glycidyl monomethacrylate, glycidyl dimethacrylate, glycidyl methacrylate, allyl glycidyl ether, and t-Butyl glycidyl ether.
  • the tensile strength of the compatibilized plastic material disclosed herein is at least 20MPa.
  • the flexural modulus is within the range of 600MPa and 2000MPa; at times, between about 600 MPa to about 820 MPa; at times, between about 800 MPa to about 1020 MPa; at times, between about 1000 MPa to about 1220 MPa; at times, between about 1200 MPa to about 1420 MPa; at times between about 1400 MPa to about 1620 MPa; at times, between about 1600 MPa to about 1820 MPa; at times, between about 1800 MPa to about 2000 MPa.
  • the compatibilized plastic material is characterized by its Tensile Elongation.
  • Tensile elongation which is a measurement of the percentage increase in length of a material sample when it is stretched to its breaking point during a tensile test, can be determined using ISO 527 or ASTM D638 standards as further described below in connection with the Examples, which form an integral part of the present disclosure.
  • the tensile elongation of the compatibilized plastic material disclosed herein is at least 5%.
  • the tensile elongation of the presently disclosed compatibilized plastic material is within the range of 10% and 400%; at times between about 20% to about 75%; at times between about 70% to about 125%; at times between about 120% to about 175%; at times between about 170% to about 225%; at times between about 220% to about 275%; at times between about 270% to about 400%.
  • tie layer refers to an intermediate layer that is used to bond or "tie” together two incompatible materials or polymers that would otherwise have poor adhesion or compatibility with each other. It acts as a bridge between two dissimilar materials, promoting adhesion and enhancing the overall performance of a multilayered structure.
  • the at least one non-polyolefin in the article of manufacture is selected from the group consisting of polyamide, polyester, EVOH, polyacrylate, polycarbonate, polystyrene, and polyurethane Polyethylene terephthalate (PET), Polyvinyl chloride (PVC), Polystyrene (PS), Polyethylene oxide (PEO), Polyurethane (PU), Polycarbonate (PC), Polyethylene glycol (PEG), Poly(methyl methacrylate) (PMMA), Polyvinylidene fluoride (PVDF), Polyamide (PA/Nylon), Polyimide (PI), Polyethylene naphthalate (PEN), Polybutadiene (PBD), Polyphenylene oxide (PPO), Polysulfone (PSU), Polyethylene terephthalate glycol (PETG), Poly ether etherketone (PEEK), Polyacrylonitrile (PAN), Polyvinyl acetate (PVAc), Polyvinyl alcohol
  • vitrimer includes one or more vitrimers as defined and disclosed herein.
  • PE-g-GMA Glycidyl-methacrylate-grafted polyethylene (PE-g-GMA) (Lotader AX8840 with 8 wt% GMA groups) was purchased from Arkema, France.
  • rPP Recycled Polypropylene
  • Multilayer films comprising layers of PET, EVOH, polyamide, polyolefin, polyurethane were supplied as post-industrial waste by Plastopil HaZorea Ltd., Israel.
  • a P-Hydroxy Ester (BHE) composition was prepared by reactive extrusion of a glycidyl-methacrylate-grafted polyethylene (PE-g-GMA) with phthalic anhydride in a polyolefin matrix.
  • Figure l is a diagram describing a mechanism of preparing P-Hydroxy Ester (BHE).
  • composition, structure and ester bond formation were elucidated by FTIR and DSC.
  • Figure 3A shows the DSC thermograms of a neat BHE sample - 1 st heating, cooling and re-crystallization, and 2 nd heating.
  • Figure 3B shows the heating/cooling thermograms of BHE-Moprylene (5:95 wt:wt) mixture.
  • Figure 3C shows the heating/cooling thermograms of BHE-SW75 (5:95 wt:wt) mixture.
  • Figure 3D shows the heating/cooling thermograms of SW-Bigbagim-BHE mixture (47.5:47.5:5 wt:wt:wt). “Bigbagim” are recycled PE:PP plastic bags from the construction industry.
  • Figures 3A-3D show the melting peaks during 1 st heating cycle, the crystallization peaks during cooling, and the re-melting peaks during 2 nd heating cycle.
  • the BHE composition as in Example 1 was used to compatibilize blends of Virgin Polypropylene (vPP) and Recycled Polypropylene (rPP).
  • 95 wt% of mixed polyolefins were dry -mixed with 5 wt% of BHE components (95 wt% PE-g-MA, 3.8 wt% PA and 1.2 wt% Zn(CH 3 COO) 2 .
  • the mixture was then compounded in a PRISM twin screw extruder (L ⁇ D 40) at 190 °C, 200 RPM.
  • compositions of some of the blends are given in Table 1 and Table 3.

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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)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente divulgation concerne un vitrimère comprenant au moins deux squelettes de polyoléfine, au moins l'un des au moins deux squelettes de polyoléfine étant relié, au moins une fois, à un autre squelette de polyoléfine des au moins deux squelettes de polyoléfine, ladite liaison se faisant par l'intermédiaire d'un pont contenant un diester. La divulgation concerne en outre un procédé d'obtention d'un vitrimère, et un procédé de compatibilisation d'un polymère utilisant le vitrimère. En outre, la présente divulgation concerne un mélange polymère homogène comprenant au moins deux polymères synthétiques et le vitrimère divulgué, ainsi qu'un article manufacturé comprenant le vitrimère ou le mélange polymère homogène.
PCT/IL2024/050721 2023-07-26 2024-07-23 Vitrimères, leurs procédés de production et leurs utilisations pour la compatibilisation de mélanges de polymères Pending WO2025022386A1 (fr)

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US202363515656P 2023-07-26 2023-07-26
US63/515,656 2023-07-26

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018028365A1 (fr) 2016-08-09 2018-02-15 翁秋梅 Polymère dynamique à réseau réticulé hybride, et application associée
WO2020142578A1 (fr) 2019-01-02 2020-07-09 Board Of Trustees Of Michigan State University Composition omniphobe autonettoyante et auto-cicatrisante, articles associés et procédés associés
WO2020160089A1 (fr) 2019-01-31 2020-08-06 Board Of Trustees Of Michigan State University Composition stratifiée autocicatrisante, articles et procédés associés
CN112126150A (zh) * 2020-09-27 2020-12-25 上海交通大学 可循环使用的POE vitrimer弹性体、发泡材料及其制备方法和应用
CN113337234A (zh) 2021-05-14 2021-09-03 武汉理工大学 一种常温固化环氧树脂基vitrimer胶黏剂及其制备方法
US20220162402A1 (en) * 2020-11-24 2022-05-26 Board Of Trustees Of Michigan State University Thermally reversibile crosslinked polyolefins and related polymers, and related methods
WO2022268662A1 (fr) * 2021-06-25 2022-12-29 Sabic Global Technologies B.V. Polymères vitrimères dérivés de polyoléfines fonctionnalisées

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WO2018028365A1 (fr) 2016-08-09 2018-02-15 翁秋梅 Polymère dynamique à réseau réticulé hybride, et application associée
WO2020142578A1 (fr) 2019-01-02 2020-07-09 Board Of Trustees Of Michigan State University Composition omniphobe autonettoyante et auto-cicatrisante, articles associés et procédés associés
WO2020160089A1 (fr) 2019-01-31 2020-08-06 Board Of Trustees Of Michigan State University Composition stratifiée autocicatrisante, articles et procédés associés
CN112126150A (zh) * 2020-09-27 2020-12-25 上海交通大学 可循环使用的POE vitrimer弹性体、发泡材料及其制备方法和应用
US20220162402A1 (en) * 2020-11-24 2022-05-26 Board Of Trustees Of Michigan State University Thermally reversibile crosslinked polyolefins and related polymers, and related methods
CN113337234A (zh) 2021-05-14 2021-09-03 武汉理工大学 一种常温固化环氧树脂基vitrimer胶黏剂及其制备方法
WO2022268662A1 (fr) * 2021-06-25 2022-12-29 Sabic Global Technologies B.V. Polymères vitrimères dérivés de polyoléfines fonctionnalisées

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KAR GOUTAM PRASANNA ET AL: "Scalable upcycling of thermoplastic polyolefins into vitrimers through transesterification", JOURNAL OF MATERIALS CHEMISTRY A, vol. 8, no. 45, 27 October 2020 (2020-10-27), GB, pages 24137 - 24147, XP055871452, ISSN: 2050-7488, DOI: 10.1039/D0TA07339C *
R.W. CLARKET. SANDMEIERK.A. FRANKLIN: "Dynamic crosslinking compatibilizes immiscible mixed plastics", NATURE, vol. 616, pages 731 - 739
Z. BAUER: "Compatibilization of Polymer Blends Utilizing Vitrimer Chemistry", M.SC. THESIS, 2022
Z. P. ZHANGM. Z. RONGM. Q. ZHANG: "Polymer engineering based on reversible covalent chemistry: A promising innovative pathway towards new materials and new functionalities", PROGRESS IN POLYMER SCIENCE, vol. 80, 2018, pages 39 - 93, XP085382023, DOI: 10.1016/j.progpolymsci.2018.03.002

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