Synthesis of PMMA Microparticles with a Narrow Size Distribution by Photoinitiated RAFT Dispersion Polymerization with a Macromonomer as the Stabilizer

Tan, Jianbo; Zhao, Guangyao; Lu, Yijie; Zeng, Zhaohua; Winnik, Mitchell A.

doi:10.1021/ma501432s

Cited by 40 publications

(32 citation statements)

References 36 publications

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“…Markedly, even though AND4 alone, AND4/R‐CL or AND4/Iod were inefficient, the AND4 based three‐component systems (AND4/Iod/NVK or AND4/MDEA/R‐CL) initiated the free radical photopolymerization of TMPTA but with lower conversions (i. e. 36 % and 48 %, respectively). This results from the formation of new radicals as illustrated in the following reactions (R6–R10) as in related 1–8 naphthalimides . Finally (Figure , Table ), the efficiency of the AND based PISs is slightly higher than that of BAPO (62–64 % vs. 56 %) and noticeably higher compared to CQ/amine (50–58 % vs. 35 %).

true Ph^{•} + NVK \to Ph - NVK^{•}

true Ph - NVK^{•} + Ph_{2} normalI^{+} \to Ph - NVK^{+} + Ph^{•} + Ph - normalI

true AND^{•}^{+} + MDEA \to AND + MDEA^{•}^{+} \to AND + normalH^{+} + MDEA_{(- normalH)}^{•}

true^{1, 3} AND + MDEA \to AND^{•}^{-} + MDEA^{•}^{+} \to AND - normalH^{•} + MDEA_{(- normalH)}^{•}

true AND^{•}^{-} (o r A N D - H^{•}) + normalR - Cl \to AND (o r A N D + H^{+}) + (R - Cl)^{•}^{-}

…”

Section: Resultsmentioning

confidence: 84%

“…Under light irradiation, ANDs are promoted from their ground states to their excited states and interact with the other compounds (e. g. Ph 2 I + or R‐Cl) to generate reactive species (i. e. cations and radicals) as illustrated in the following reactions (R1–R4) as in related compounds:,,

true^{1, 3} AND + Ph_{2} normalI^{+} \to AND^{•}^{+} + Ph_{2} normalI^{•}

true Ph_{2} normalI^{•} \to Ph^{•} + Ph - normalI

true^{1, 3} AND + normalR - Cl \to AND^{•}^{+} + (R - Cl)^{•}^{-}

true (R - Cl)^{•}^{-} \to normalR^{•} + Cl^{-}

…”

Section: Resultsmentioning

confidence: 99%

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Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

et al. 2018

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The photochemical mechanism of the radical generation from photoinitiating systems based on 1, 8‐naphthalimide derivatives (ANDs; with tertiary amine moieties) are investigated by using various approaches including cyclic voltammetry, steady‐state photolysis, and electron spin resonance spin‐trapping techniques. It reveals that radicals can be produced from ANDs alone or ANDs/additive (e. g. iodonium salt or chloro triazine) combinations. The generated radicals and cations can initiate both free‐radical and cationic photopolymerization reactions under irradiation with various light‐emitting diodes or a halogen lamp. For most of the AND‐based photoinitiating systems, more than 60 % of acrylate or epoxide conversions were attained, and were even higher than those obtained by using commercial photoinitiators, for example, bisacylphosphine oxide or camphorquinone. More interestingly, the AND1‐based photoinitiating system can also initiate concomitant cationic/radical polymerizations and can be used for the synthesis of interpenetrated polymer networks.

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true Ph^{•} + NVK \to Ph - NVK^{•}

true Ph - NVK^{•} + Ph_{2} normalI^{+} \to Ph - NVK^{+} + Ph^{•} + Ph - normalI

true AND^{•}^{+} + MDEA \to AND + MDEA^{•}^{+} \to AND + normalH^{+} + MDEA_{(- normalH)}^{•}

true^{1, 3} AND + MDEA \to AND^{•}^{-} + MDEA^{•}^{+} \to AND - normalH^{•} + MDEA_{(- normalH)}^{•}

true AND^{•}^{-} (o r A N D - H^{•}) + normalR - Cl \to AND (o r A N D + H^{+}) + (R - Cl)^{•}^{-}

…”

Section: Resultsmentioning

confidence: 84%

true^{1, 3} AND + Ph_{2} normalI^{+} \to AND^{•}^{+} + Ph_{2} normalI^{•}

true Ph_{2} normalI^{•} \to Ph^{•} + Ph - normalI

true^{1, 3} AND + normalR - Cl \to AND^{•}^{+} + (R - Cl)^{•}^{-}

true (R - Cl)^{•}^{-} \to normalR^{•} + Cl^{-}

…”

Section: Resultsmentioning

confidence: 99%

Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

et al. 2018

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“…To expand these approaches to particular applications where the reactions need to be conducted at low temperatures (e.g., polymerization of monomers with low ceiling temperatures or biochemical applications), a photoinduced radical polymerization process becomes an excellent candidate . Many works have recently been reported in this field such as photo‐ATRP 69, or photo‐RAFT . The CuCs‐based PISs proposed so far are capable of initiating photo‐ATRP.…”

Section: Copper Complexes As Photoinitiators Of Controlled Radical Pomentioning

confidence: 99%

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

Xiao

Zhang

Campolo

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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International audienceThe utilization of visible lights for the fabrication of polymeric materials is recognized as a promising and environmentally friendly approach. This process relies on the photochemical generation of reactive species (e.g., radicals, radical cations, or cations) from well-designed photoinitiators (PIs) or photoinitiating systems (PISs) to initiate the polymerization reactions of different monomers (acrylates, methacrylates, epoxides, and vinyl ethers). In spite of the fact that metal complexes such as ruthenium- or iridium-based complexes have found applications in organic and polymer synthesis, the search of other low-cost metal-based complexes as PISs is emerging and attracting increasing attentions. Particularly, the concept of the photoredox catalysis has appeared recently as a unique tool for polymer synthesis upon soft conditions (use of light emitting diodes and household lamp). This highlight focuses on recently designed copper and iron complexes as PI catalysts in the application of photoinduced polymerizations (radical, cationic, interpenetrated polymer networks, and thiol-ene) or controlled radical polymerization under visible light irradiatio

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“…40,41 The development of new polymeric materials usually requires the use of highly selective and efficient functionalization reactions. Macromonomers can be synthesized using various methods such as anionic, cationic, and radical polymerization, as well as the chemical modication of polymer ends or backbone.…”

Section: Synthesis Of Phenylamine-functionalized Poly(ethylene Glycolmentioning

confidence: 99%

AB₂ Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol) and its electrospun nanofiber blend with poly(ε-caprolactone)

et al. 2015

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This paper describes the synthesis and characterization of novel type AB 2 Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol) [PEG-b-(PANI) 2 ], and preparation of its electrospun nanofiber blend with poly(3-caprolactone) [PEG-b-(PANI) 2 /PCL]. The chemical structures of all samples as representatives were characterized by means of Fourier transform infrared (FTIR), and 1 H nuclear magnetic resonance (NMR) spectroscopies. The molecular weights of PANI segment(s), and miktoarm star conductive PEG-b-(PANI) 2 were found to be 3720, and 5847, respectively, from 1 H NMR spectroscopy. Moreover, electrical conductivities, electroactivities, thermal behaviors, morphologies, and compositions of the synthesized samples were studied. The conductivity and electroactivity measurements showed that PEG-b-(PANI) 2 and PEG-b-(PANI) 2 /PCL electrospun blend nanofibers have lower electrical conductivity and electroactivity than those of the pure PANI. However, the lower electrical conductivity and electroactivity levels in these materials can be improved at the price of solubility, processability, and biocompatibility. Field emission scanning electron microscopy (FE-SEM) images showed that the PEG-b-(PANI) 2 /PCL electrospun nanofibers have a single phase, indicating good interactions between the blend components. The average diameters of these fibers were in the size range of 70 AE 10 nm, and there was no formation of beaded structures in comparison with electrospun fibers of pure PCL. As results, we predicted the synthesized PEG-b-(PANI) 2 and PEG-b-(PANI) 2 /PCL can be used in the biomedical fields such as in conductive scaffolds to promote neurite outgrowth, and nerve regeneration.Scheme 1 Synthetic route of the AB 2 Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol).36718 | RSC Adv., 2015, 5, 36715-36726This journal is

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Synthesis of PMMA Microparticles with a Narrow Size Distribution by Photoinitiated RAFT Dispersion Polymerization with a Macromonomer as the Stabilizer

Cited by 40 publications

References 36 publications

Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

AB₂ Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol) and its electrospun nanofiber blend with poly(ε-caprolactone)

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Synthesis of PMMA Microparticles with a Narrow Size Distribution by Photoinitiated RAFT Dispersion Polymerization with a Macromonomer as the Stabilizer

Cited by 40 publications

References 36 publications

Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Copper and iron complexes as visible‐light‐sensitive photoinitiators of polymerization

AB2 Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol) and its electrospun nanofiber blend with poly(ε-caprolactone)

Contact Info

Product

Resources

About

AB₂ Y-shaped miktoarm star conductive polyaniline-modified poly(ethylene glycol) and its electrospun nanofiber blend with poly(ε-caprolactone)