Atom Transfer Radical Polymerization of Methyl Methacrylate with Polyethylene-functionalized Ligands

Liou, Shingtza; Rademacher, Jude; Malaba, Dennis; Pallack, Mical E.; Brittain, William J.

doi:10.1021/ma992095z

Cited by 66 publications

(64 citation statements)

References 13 publications

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“…[143][144][145][146] It was demonstrated that several partially fluorinated compounds, typically used in fluorous biphasic systems, show marked solubility differences in common, nonfluorinated, organic solvents as the temperature changes. 147,148 These compounds could be used as catalysts for certain chemical transformations at high-temperature (homogeneous conditions), and upon completion of the reaction, they could be isolated by simple cooling followed by filtration; no fluorinated solvents were required in the process.…”

Section: Introductionmentioning

confidence: 99%

“Green” Atom Transfer Radical Polymerization: From Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials

2007

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Section: Introductionmentioning

confidence: 99%

“Green” Atom Transfer Radical Polymerization: From Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials

2007

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“…[16] Another strategy was presented by Brittain et al who reported the first soluble polymer support based on amino functionalized polyethylene, that was modified with pyridine 2-carboxy aldehyde. [17] Results of ATRP with methyl methacrylate revealed good control over molecular weight of the resulting polymers, however deviation from the first order-plot was observed and low reactivity (92% monomer conversion at 100 8C after 26 h). Despite the advances that have been made in the past ten years in the development of new immobilization techniques and support materials for transition-metal catalysts on the one hand and being able to transfer an increasing number of transition-metal catalyzed polymerizations into aqueous media on the other hand, there has been little effort made to combine these two approaches.…”

Section: Introductionmentioning

confidence: 91%

Direct and Reverse ATRP of MMA in Aqueous Dispersed Medium in the Presence of a Bipyridine‐Functionalized Block Copolymer Support

Kotre

Nuyken

Weberskirch

2004

Macro Chemistry & Physics

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Summary: In a recent communication (Macromol. Rapid Commun. 2002, 23, 871), we reported the synthesis of a bipyridine containing amphiphilic polymer and its usage as macroligand in the atom transfer radical polymerization (ATRP) of MMA in aqueous dispersed medium. Investigations on the mechanism and locus of nucleation by transmission electron microscopy (TEM) studies herein of latex particles prepared by direct ATRP using oil‐soluble ethyl 2‐bromoisobutyrate as initiator revealed a broad particle size distribution between 250 nm and 1 μm, suggesting two nucleation sites, micelles and monomer droplets. By using the water‐soluble initiator 2,2′‐azoisobutyramidine‐dihydrochloride (V‐50) reverse ATRP experiments were conducted at 90 °C. Kinetic measurements showed a sigmoidal slope of monomer conversion versus time as a first indication for an emulsion‐like process. Controlled polymerization behavior was achieved at a ratio of radicals versus Cu(II) deactivator of 1:8. TEM measurements of polymer latex particles obtained by reverse ATRP revealed particle sizes between 100 and 400 nm. Residual copper content of eight PMMA samples prepared by direct and reverse ATRP was determined to be 0.01–0.03 wt.‐% (theoretical 0.73 wt.‐%) and indicated that on average 96–99% of all copper used in a polymerization experiment can be removed from the polymer latex particles by a simple precipitation/washing step.Direct and reverse ATRP experiments of MMA in aqueous media in the presence of an amphiphilic, water‐soluble block copolymer with pendent bipyridine units.magnified imageDirect and reverse ATRP experiments of MMA in aqueous media in the presence of an amphiphilic, water‐soluble block copolymer with pendent bipyridine units.

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“…Soluble supports based on functionalized polyethylene chains therefore were utilized, exploiting the solubility of low-molecular-weight polyethylene in toluene at high temperature. [11] However, the polymerization rates were lower and polydispersity indices of the PMMA synthesized were in the range 1.4-1.5. This is attributed to the low probability of three oligomer/polymer chains (two PE ligands and one growing chain) taking part in the activation-deactivation cycle.…”

Section: Introductionmentioning

confidence: 97%

Atom Transfer Radical Polymerization Using Multidentate Amine Ligands Supported on Soluble Hyperbranched Polyglycidol

Kumar

Kizhakkedathu

Brooks

2004

Macro Chemistry & Physics

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Summary: Controlled polymerization of styrene in toluene was achieved by atom transfer radical polymerization (ATRP) using hyperbranched polyglycidol‐supported multidentate amine ligands/CuIBr catalyst systems. These catalyst systems with nanoscopic dimensions were more active than the corresponding low‐molecular‐weight ligands. The controlled/living nature of the polymerization is supported by linear first order plots (ln[M]o/[M] versus time) and a linear increase of $\overline M _{\rm n}$ versus conversion as well as low polydispersity. Similar controlled polymerization of methyl methacrylate was possible in acetonitrile. Up to 97% of total copper used for polymerization could be removed from the polymer by simple precipitation in methanol and filtration.Molecular weight characteristics for styrene polymerization using PG‐triamine as a ligand.magnified imageMolecular weight characteristics for styrene polymerization using PG‐triamine as a ligand.

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Atom Transfer Radical Polymerization of Methyl Methacrylate with Polyethylene-functionalized Ligands

Cited by 66 publications

References 13 publications

“Green” Atom Transfer Radical Polymerization: From Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials

“Green” Atom Transfer Radical Polymerization: From Process Design to Preparation of Well-Defined Environmentally Friendly Polymeric Materials

Direct and Reverse ATRP of MMA in Aqueous Dispersed Medium in the Presence of a Bipyridine‐Functionalized Block Copolymer Support

Atom Transfer Radical Polymerization Using Multidentate Amine Ligands Supported on Soluble Hyperbranched Polyglycidol

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