Homogeneous reverse atom transfer radical polymerization of glycidyl methacrylate and ring-opening reaction of the pendant oxirane ring

Li, Gang; Zhu, Xiulin; Zhu, Jian; Cheng, Zhenping; Zhang, Wei

doi:10.1016/j.polymer.2005.10.061

Cited by 42 publications

(32 citation statements)

References 42 publications

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“…Zhu et al [18] demonstrated that well-defined poly(GMA) can be prepared using cyanopropyl dithionapthenoate as RAFT agent. Homopolymers of GMA using CuX/PMDETA [19] as catalyst and reverse ATRP conditions (AIBN and N,N, butyldithiocarbamate copper) [20] were also successfully obtained.…”

Section: Communicationmentioning

confidence: 97%

Controlled Radical Polymerization of 2,3‐Epithiopropyl Methacrylate

Sordi

Ceschi

Petzhold

et al. 2007

Macromol. Rapid Commun.

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We report first results on the controlled radical polymerization of 2,3‐epithiopropyl methacrylate (ETMA) also known as thiiran‐2‐ylmethyl methacrylate. Reversible addition‐fragmentation chain transfer (RAFT) of ETMA was carried out in bulk and in solution, using AIBN as initiator and the chain transfer agents: cyanopropyl dithiobenzoate (CPDB) and cumyl dithiobenzoate (CDB). A linear increase of the number‐average molecular weight and decrease of the polydispersity with monomer conversion were observed using CPDB as transfer agent, indicating a controlled process. Atom transfer radical polymerization (ATRP) of ETMA was performed under different reaction conditions using copper bromide complexed by tertiary amine ligands and ethyl 2‐bromoisobutyrate (EBiB) or 2‐bromopropionitrile (BPN) as initiator. All experiments lead to a crosslinked polymer. Preliminary studies in the absence of initiator showed that the CuBr/ligand complex alone initiates the ring‐opening polymerization of thiirane leading to a poly(propylene sulfide) with pendant methacrylate groups.magnified image

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Section: Communicationmentioning

confidence: 97%

Controlled Radical Polymerization of 2,3‐Epithiopropyl Methacrylate

Sordi

Ceschi

Petzhold

et al. 2007

Macromol. Rapid Commun.

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“…ATRPs of different monomers as indicated in Figure 15, including lauryl methacrylate [87], hexadecyl acrylate [88], glycidyl methacrylate (GMA) [89], 6-(4-phenylazophenoxy) hexylmethacrylate [90], and 6-(4-methoxy-4-oxy-azobenzene) hexyl methacrylate [91], were carried out and functional homopolymers were obtained. The results showed wellcontrolled polymerization behaviors for all the monomers: a linear molecular weight increase with monomer conversion and narrow molecular weight distributions.…”

Section: Functional Polymers Prepared Via Controlled/ "Living" Radicamentioning

confidence: 99%

“…In our case, by the reaction with diphenylphosphinic chloride, the obtained polymers showed enhanced thermal stability. For the azobenzene containing polymers, surface relief gratings (SRGs) with efficient diffraction were observed with a linearly krypton polarized laser irradiation [89].…”

Section: Functional Polymers Prepared Via Controlled/ "Living" Radicamentioning

confidence: 99%

Mechanism study and molecular design in controlled/“living” radical polymerization

Tu¹,

Cheng²,

Zhang³

et al. 2010

Sci. China Chem.

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This tutorial review summarizes recent progress in the research field of controlled/"living" radical polymerization (CLRP) from Soochow University. The present paper gives a broad overview of the mechanism study and molecular design in CLRP. The mechanism study in CLRP aided by microwave, initiated by -radiation at low temperature, mediated by iron, in reversible addition-fragmentation chain transfer (RAFT) polymerization and the mechanism transfer between different CLRP processes are reviewed and summarized. The molecular design in CLRP, especially in RAFT polymerization for mechanism study, and in achieving tailor-made functional polymers is studied and discussed in the later part.controlled/"living" radical polymerization, atom transfer radical polymerization, reversible addition-fragmentation chain transfer polymerization, molecule design, mechanism study

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“…The other ring-opening reaction, hydrolysis, transforms the epoxide groups into glycerol (bis-alcohol) groups [6,7]. The poly(glycidyl methacrylate)s (PGMAs) were also modified by phosphonation with diphenylphosphinic chloride [8], and silylation with tris(trimethylsilyl) methyl lithium [9], whereas the reaction with monothiol-functionalized polyhedral silsesquioxane yielded the cage-like inorganic materials in an organic cylindrical matrix [10]. The grafting reactions via epoxy groups in the short PGMA segment in block copolymers were achieved with silanol functionality of silica nanoparticles [11], or aminosililated quartz wafer surfaces [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and self-assembly behavior of amphiphilic methyl α-D-glucopyranoside-centered copolymers

2014

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A series of well-defined polymers with various content of reactive oxirane groups (25-100 mol%) were synthesized via atom transfer radical polymerization (ATRP). The acetal derivatives of methyl α-D-glucopyranoside used as bi-, tri-, and tetrafunctional initiators allowed us to design macromolecules containing a sugar moiety in the center with V-and star-shaped topologies, and a length of each polymethacrylate segment in the range of 30-75 units. Various degrees of oxirane ring opening via aminolysis with mono-and diamines (20-100 %) or azidation (100 %) have demonstrated that the reactivity of pendant epoxide groups incorporated into the polymer was strongly dependent on the nucleophile agent and reaction environment. The complete transformation in the reaction with ethylenediamine and sodium azide yielded amphiphilic copolymers with differential solubility (diaminefunctionalized polymers in polar protic solvents, e.g., water, versus azide-functionalized polymers in polar aprotic solvents, e.g., dimethylformamide). A few polymeric forms, that is unimers (0.5-1 nm), micelles (5-30 nm), aggregates (170-290 nm) and superaggregates (> 4,500 nm), were indicated by DLS measurements of water-soluble ethylenediamine derivatives of copolymers. Both the epoxy-functionalized polymers and their modified derivatives are potential materials for biomedical applications.

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Homogeneous reverse atom transfer radical polymerization of glycidyl methacrylate and ring-opening reaction of the pendant oxirane ring

Cited by 42 publications

References 42 publications

Controlled Radical Polymerization of 2,3‐Epithiopropyl Methacrylate

Controlled Radical Polymerization of 2,3‐Epithiopropyl Methacrylate

Mechanism study and molecular design in controlled/“living” radical polymerization

Synthesis and self-assembly behavior of amphiphilic methyl α-D-glucopyranoside-centered copolymers

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