RAFT polymerization, characterization, and post-polymerization modification of a copolymer of vinylbenzyl chloride: Towards thiolate functionalized copolymers

Faghihi, Farhad; Hazendonk, Paul

doi:10.1016/j.polymer.2017.08.067

Cited by 10 publications

(6 citation statements)

References 32 publications

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“…π–π interactions between two aromatic compounds, urea functionality, and S–S cross-linked thiols are versatile substituents to interact with each other, producing a tailor-made cross-linking polymer with tunable bulk properties. Use of a reactive terminal moiety (e.g., alkyl, alkyne, halide, and epoxy group) is a prerequisite for the introduction of an additional functional group. The important and efficient click chemistry techniques, such as thiol–ene, alkyne–azide cycloaddition, Michael addition, Diels–Alder, epoxide-amine reactions, and so forth are facile with high conversion ratios.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Preparation of Cross-linked Films with Ester-Free Poly(trimethylene carbonate) Bearing Aromatic Urea Moiety

et al. 2021

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In an attempt to develop medical materials, a new design of ester-free poly(trimethylene carbonate) (PTMC) derivatives incorporating an aromatic pendant and urea moiety is explored. The aim of the present research study was to assess whether a flexible, elastic, and degradable PTMC film can promote the mechanical properties and perform better than commercially available PTMC. To tune the mechanical and thermal properties, two kinds of ratio with a cross-linker and a monomer were investigated, as well as the introduction of urea moieties. Both vinyl benzyl- and urea-based films showed thermal degradation with 10% weight loss (T 10) of over 200 °C, which suggests the potential widespread use of the materials at a highly elevated temperature, such as in sterilization. The chemically modified PTMC films also have an improved glass transition temperature (T g) up to 21 °C. Moreover, the incorporation of vinyl benzyl and the cross-linker markedly enhanced the elongation, tensile strength, and hydrolysis stability after 90 days. Although the materials showed slight deformation and stiffness, the urea-functionalized film has significant effects on the swelling degree. The present research demonstrates a facile modification approach for the development of ester-free TMC derivatives.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Preparation of Cross-linked Films with Ester-Free Poly(trimethylene carbonate) Bearing Aromatic Urea Moiety

et al. 2021

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“…The VBC feeding amount could affect the morphology of the PAH/PS/PMMA- co -PVBC Janus hemisphere, showing larger patches with more VBC being utilized (Figure S4). The polymerization rate of VBC is higher than that of MMA, promoting the PMMA- co -PVBC grafted on the hemispherical surface . The PMMA- co -PVBC patches were further modified with a reported SI-ATRP method .…”

Section: Resultsmentioning

confidence: 99%

Janus Hemispheres through Controlled Polymerization-Induced Phase Separations within Wax Droplets

et al. 2023

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A series of Janus hemispheres with a patchy hemispherical surface and a flat undersurface were synthesized through controlled polymerization-induced phase separation within emulsified wax droplets. The hemispherical shape was generated through the polymerization of styrene within wax droplets, followed by the grafting of hydrophilic polymers on the exposed surface. Then, the patchy hemispherical surface was achieved after introducing the hydrophobic acrylate monomers within wax droplets and controlling the polymerization-induced phase separation. The morphological evolution of patches was recorded via the reaction time, followed by their morphological regulation through the type, feeding amount, and cross-linking degree of acrylate monomers. A functional monomer, vinyl benzyl chloride (VBC), was also used to copolymerize the patches for grafting a zwitterionic polymer via surface-initiated atom transfer radical polymerization (SI-ATRP). The as-obtained Janus hemispheres were employed to fabricate robust coatings with wettability tuned from superhydrophobicity to underwater superoleophobicity by the grafted zwitterionic polymers.

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“…Although the primary focus of research in our laboratory has traditionally been ROMP, we were interested in designing a general process that could be applied toward the functionalization of other polymers as well. Of particular interest was the modification of poly(styrene‐ co ‐vinylbenzyl chloride) sidechains, which has been carried out using a variety of nucleophiles, including sulfur‐based species . In this vein, we were curious as to whether or not reactions similar to the thio‐bromo click reactions described above could be used to modify the benzyl‐chloride‐containing copolymer 10 .…”

Section: Resultsmentioning

confidence: 99%

“…Polymerization of α-bromo ester 1 using initiator 2 and mechanochemically facilitated thio-bromo "click" reactions to form 4-8. sidechains, which has been carried out using a variety of nucleophiles, including sulfur-based species. [40][41][42][43][44] In this vein, we were curious as to whether or not reactions similar to the thio-bromo click reactions described above could be used to modify the benzyl-chloride-containing copolymer 10. To begin this study, the free radical polymerization (FRP) of styrene and 4-vinylbenzyl chloride was conducted.…”

Section: Introductionmentioning

confidence: 99%

Post‐Polymerization Thiol Substitutions Facilitated by Mechanochemistry

Ashlin

Hobbs

2019

Macro Chemistry & Physics

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The use of mechanical force to facilitate post‐polymerization, solvent‐free thiol substitution reactions is described. These reactions are amenable to halogen‐containing materials prepared using ring opening metathesis polymerization and free radical polymerization reactions. Reactions of these polymers with various thiols can be carried out in a ball mill and are complete in a matter of minutes. Further, 1H NMR and GPC analysis show no significant decomposition of the polymer chain.

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RAFT polymerization, characterization, and post-polymerization modification of a copolymer of vinylbenzyl chloride: Towards thiolate functionalized copolymers

Cited by 10 publications

References 32 publications

Synthesis and Preparation of Cross-linked Films with Ester-Free Poly(trimethylene carbonate) Bearing Aromatic Urea Moiety

Synthesis and Preparation of Cross-linked Films with Ester-Free Poly(trimethylene carbonate) Bearing Aromatic Urea Moiety

Janus Hemispheres through Controlled Polymerization-Induced Phase Separations within Wax Droplets

Post‐Polymerization Thiol Substitutions Facilitated by Mechanochemistry

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