Enzymatic miniemulsion polymerization of styrene with a polymerizable surfactant

Kohri, Michinari; Kobayashi, Ayaka; Fukushima, Haruka; Kojima, Takashi; Taniguchi, Tadatsugu; Saito, Kyoichi; Nakahira, Takayuki

doi:10.1039/c2py00542e

Cited by 30 publications

(15 citation statements)

References 48 publications

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“…Polymer particles were synthesized with 1, using the same manner of surfactants as in the case of previously synthesized C 12 DMAEMA latexes [17]. The samples were purified with a hollow fiber dialyzer using a membrane (50 nm pore size) and a tubing pump system to remove unreacted monomers and the initiator.…”

Section: Preparation Of Alkyne-bearing Pst Particles By Enzymatic Minmentioning

confidence: 99%

“…Recently, we demonstrated the preparation of polymer particles by enzymatic miniemulsion polymerization with a cationic surfmer, i.e., N,N-dimethyl-N-n-dodecyl-N-2-methacryloyloxyethyl ammonium bromide (C 12 DMAEMA) [17]. Enzymatic miniemulsion polymerization is a practical method for the preparation of relatively monodisperse polymer particles, because the approach involved a mild enzymatic process at room temperature.…”

Section: Introductionmentioning

confidence: 99%

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A Green Approach for the Synthesis of Fluorescent Polymer Particles by Combined Use of Enzymatic Miniemulsion Polymerization with Clickable Surfmer and Click Reaction

Kohri

Kobayashi

Nannichi

et al. 2014

Trans. Mat. Res. Soc. Japan

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Herein, we describe a facile and green method to prepare fluorescent polymer particles by combined use of enzymatic miniemulsion polymerization and click reaction. Firstly, alkyne-bearing polymer particles were prepared by HRP-mediated miniemulsion polymerization of styrene with clickable surfmer (surfactant + monomer) 1. Then, azide-bearing fluorescence compound, i.e., dansyl azide compound 2, was introduced to polymer particles surface via click reaction using Cu(I) catalyst. This methodology will be applied to a broad range of azide-bearing compounds to generate functional polymer particles. Since both enzymatic miniemulsion polymerization and click reaction are conducted at room temperature in water, present method offers a practical and environmental friendly method for preparation of functional polymer particles.

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Section: Preparation Of Alkyne-bearing Pst Particles By Enzymatic Minmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Green Approach for the Synthesis of Fluorescent Polymer Particles by Combined Use of Enzymatic Miniemulsion Polymerization with Clickable Surfmer and Click Reaction

Kohri

Kobayashi

Nannichi

et al. 2014

Trans. Mat. Res. Soc. Japan

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“…A more in-depth study of that system was conducted by Kohri et al [17,18]. These authors investigated the influence of the type of surfactant, the type of β-diketone, the ratio of pentanedione/H 2 O 2 , the ratio of H 2 O 2 /HRP on the conversion of styrene, the molecular weight of the polymer and the activity of the enzyme.…”

Section: Enzyme Located In the Continuous Phasementioning

confidence: 99%

Enzymatic Catalysis at Interfaces—Heterophase Systems as Substrates for Enzymatic Action

Weiss

Landfester

2013

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Several important enzymatic reactions occurring in nature, such as, e.g., the digestion of fat, proceed only at the interface of two immiscible phases. Typically, these systems consist of an organic substrate, dispersed in an aqueous continuous phase, with a specialized enzyme capable of working at the interface. For adopting such a system for organic synthesis, a stable heterophase system with a large interfacial area is required. These prerequisites can be found in so-called miniemulsions. Such liquid-liquid heterophase systems feature droplets with sizes smaller than 500 nm, and more importantly, these emulsions do not suffer from Ostwald ripening, as conventional emulsions do. Consequently, the droplets show long-term stability, even throughout reactions conducted in the droplets. In this review, we will briefly discuss the physicochemical background of miniemulsions, provide a comprehensive overview of the enzymatically catalyzed reactions conducted in miniemulsions and, as data are available, to compare the most important features to conventional systems, as reverse microemulsions, (macro)emulsions and solvent-based systems.

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“…Although the HRP activity decreased in the presence of C 12 -DMAEMA (vide supra), this will not affect the polymerization efficiency because C 12 -DMAEMA is polymerized near the surface of monomer droplets in the initial stage of polymerization, as suggested by GPC measurements of the obtained particles, which had different reaction times. 6 Thus, desorption of C 12 -DMAEMA was suppressed and caused increasing monomer conversion, and, as a result, high-efficiency polymerization was achieved (Figure 3c). …”

mentioning

confidence: 96%

“…Very recently, we successfully demonstrated the preparation of polystyrene particles by enzyme-mediated miniemulsion polymerization with a polymerizable surfactant, i.e., N,N-dimethyl-N-n-dodecyl-N-2-methacryloyloxyethylammonium bromide (C 12 -DMAEMA), 5 using an HRP/H 2 O 2 /ACAC system in water. 6 That report described how enzymatic miniemulsion polymerization could be used as a practical method for the preparation of relatively monodisperse polymer particles, because the approach involved a mild enzymatic process at room temperature. However, the use of surfactants other than C 12 -DMAEMA was not examined, and the role of C 12 -DMAEMA in enzymatic miniemulsion polymerization has not yet been made clear.…”

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confidence: 99%

Effect of Surfactant Type on Enzymatic Miniemulsion Polymerization Using Horseradish Peroxidase as a Catalyst

et al. 2012

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The influence of surfactant type on monomer conversion and particle size of polystyrene particles prepared by horseradish peroxidase (HRP)-mediated miniemulsion polymerization was investigated.Miniemulsion polymerization is a versatile tool for synthesizing polymer particles. In principle, the stability of oil-in-water miniemulsions is attained by the use of a surfactant and a highly water-insoluble molecule (a so-called hydrophobe). Miniemulsions are produced by high-energy homogenization, and they usually yield stable and narrowly distributed monomer droplets; the polymerization of miniemulsions provides polymer particles of diameter 50500 nm. 1A horseradish peroxidase (HRP)-catalyzed redox system was reported to initiate vinyl polymerization of various monomers, e.g., acrylamide, 2 methyl methacrylate, 3 and styrene derivatives, 4 in which acetylacetone (ACAC) was adopted as a substrate for HRP to generate radicals in the presence of hydrogen peroxide (H 2 O 2 ). Very recently, we successfully demonstrated the preparation of polystyrene particles by enzyme-mediated miniemulsion polymerization with a polymerizable surfactant, i.e., N,N-dimethyl-N-n-dodecyl-N-2-methacryloyloxyethylammonium bromide (C 12 -DMAEMA), 5 using an HRP/H 2 O 2 /ACAC system in water.6 That report described how enzymatic miniemulsion polymerization could be used as a practical method for the preparation of relatively monodisperse polymer particles, because the approach involved a mild enzymatic process at room temperature. However, the use of surfactants other than C 12 -DMAEMA was not examined, and the role of C 12 -DMAEMA in enzymatic miniemulsion polymerization has not yet been made clear. It would be interesting to investigate the effect of surfactant type because the surfactant affects the polymerization efficiency and many performance properties of the resulting particles.In this study, the influence of the surfactant type on the enzymatic miniemulsion polymerization efficiency is discussed. Comparisons of four surfactants®anionic surfactant: sodium dodecyl sulfate (SDS), cationic surfactant: cetyltrimethylammonium bromide (CTAB), nonionic surfactant: polyoxyethylene lauryl ether (Emulgen 109P), and cationic polymerizable surfactant: C 12 -DMAEMA®were conducted for enzymatic miniemulsion polymerization (Figure 1). The effects of surfactant type on styrene conversion and particle size were investigated. To clarify the role of the surfactant in the enzymatic reaction, HRP activities in the presence of surfactants were also examined.Latexes were synthesized with SDS, CTAB, or Emulgen 109P, using the same molar amounts of surfactants as in the case of previously synthesized C 12 -DMAEMA latexes (The details of the synthetic procedure are shown in the Supporting Information.

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Enzymatic miniemulsion polymerization of styrene with a polymerizable surfactant

Cited by 30 publications

References 48 publications

A Green Approach for the Synthesis of Fluorescent Polymer Particles by Combined Use of Enzymatic Miniemulsion Polymerization with Clickable Surfmer and Click Reaction

A Green Approach for the Synthesis of Fluorescent Polymer Particles by Combined Use of Enzymatic Miniemulsion Polymerization with Clickable Surfmer and Click Reaction

Enzymatic Catalysis at Interfaces—Heterophase Systems as Substrates for Enzymatic Action

Effect of Surfactant Type on Enzymatic Miniemulsion Polymerization Using Horseradish Peroxidase as a Catalyst

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